| Nadia Batson | | Performing Arts | | Trinidad & Tobago | 2023 Dr. Slinger “The Mighty Sparrow” SUNSHINE Award for Contribution to the Performing Arts. | 2023 |
| Gamal “Skinny Fabulous” Doyle | | Performing Arts | | St. Vincent & The Grenadines | 2023 Dr. Hollis “Chalkdust” Liverpool SUNSHINE Award for Contribution to the Performing Arts | 2023 |
| Dr. Doreen J. Kitchens | | Jazz Music | | United States | 2023 SUNSHINE Awards for Contribution to the Performing Arts | 2023 |
| Rimli Roy | | Performing Arts | | India | 2023 SUNSHINE Awards for contribution to the Performing Arts | 2023 |
| Ron Reid | | Performing Arts | | Trinidad and Tobago | 2023 SUNSHINE Award for Contribution to Education and the Performing Arts | 2023 |
| Alvin Daniell | Education and the Performing Arts | Education and the Performing Arts | | Trinidad & Tobago | 2023 SUNSHINE Awards for Contribution to Education and the Performing Arts | 2023 |
| Natu Camara | African Music | Performing Arts | | Ivory Coast / Guinea | 2023 SUNSHINE Award for Contribution to the Performing Arts | 2023 |
| Gerardo Contino | Performing Arts | The Performing Arts | | Cuba | 2023 SUNSHINE Awards for Contribution to the Performing Arts | 2023 |
| Partrick “Eze” Rockcliffe | Special Award | Performing Arts | | Guyana | 2023 SUNSHINE Award for Contribution to the Performing Arts | 2023 |
| Dr. Shakuntala Haraksingh-Thilsted | Contribution to Research and Science | Research and Science | | Trinidad & Tobago | SUNSHINE Award for Contribution to Research and Science | 2021 |
| Ainsworth Mohammed | Contribution to the Performing Arts | Friend of the Arts | | Trinidad & Tobago | SUNSHINE Award for Contribution to the Performing Arts | 2021 |
| Sir. Selvyn Walter | Contribution to the Performing Arts – Posthumously | Friend of the Arts | | Antigua | SUNSHINE Award for Contribution to the Performing Arts | 2021 |
| Judge Vern Hodge | Contribution to Education | Education | | St. Thomas, VI | The SUNSHINE Award for Contribution to Education | 2021 |
| Kassav Band | Contribution to the Performing Arts | Performing Arts | | France/French Antilles | SUNSHINE Award for Contribution to the Performing Arts | 2021 |
| Ian Estwick | Contribution to the Arts | Friend of the Arts | | Barbados | Friend of the Arts SUNSHINE Award | 2021 |
| Dr. Oluyinka O. Olutoye | Contribution to Medicine and Science | SUNSHINE Award | | Nigeria | 2021 SUNSHINE Award | 2021 |
| Stedson “Red Plastic Bag” Wiltshire | The Performing Arts | SUNSHINE Awards Hall of Fame | | Barbados | Yes | 2019 |
| Albert Laveau | The Performing Arts | SUNSHINE Awards Hall of Fame | | Trinidad & Tobago | Yes | 2019 |
| Johnny Thomas | Friend of the Arts | SUNSHINE Awards Friend of the Arts | | Trinidad & Tobago | Yes | 2019 |
| Robert Amar | Friend of the Arts | SUNSHINE Awards Friend of the Arts | | Trinidad & Tobago | Yes | 2019 |
| Dr Erold Hinds | Friend of the Arts | SUNSHINE Awards Friend of the Arts | | Barbados | Yes | 2019 |
| Timothee “King Tmo” van-Heyningen | The Performing Arts | SUNSHINE Awards Performing Arts | | Saint Martin/Sint Maarten | Yes | 2019 |
| Darryl “Farmer Nappy” Henry | The Performing Arts | SUNSHINE Award for the Performing Arts | | Trinidad & Tobago | Yes | 2019 |
| Jean Appolon | Performing Arts | SUNSHINE Award for the Performing Arts | | Haiti | Yes | 2019 |
| Dr Andre Cropper | Education & Technology | SUNSHINE Award for Education & Technology | | Trinidad & Tobago | Yes | 2019 |
| Dr Gladys West | Education and Technology | SUNSHINE Award for Educ | | United States | Yes | 2019 |
| Etienne Charles | The Performing Arts | SUNSHINE Award for the Performing Arts | | Trinidad & Tobago | Yes | 2018 |
| Frandy Jean | Fine Arts | SUNSHINE Award for Fine Arts | | Haiti | Yes | 2018 |
| Dil-E-Nadan Band | The Performing Arts | SUNSHINE Award for the Performing Arts | | Trinidad & Tobago | Yes | 2018 |
| Bailo Bah | Performing Arts | SUNSHINE Awards for contribution to the Performing Arts | | Guinea West Africa | Yes | 2018 |
| Ricky & Angie Lord | The SUNSHINE Awards Corporate Award | The SUNSHINE Awards Corporate Award | | Trinidad & Tobago | Yes | 2018 |
| Kenneth DeSilva | Friend of the Arts | The SUNSHINE Awards Hall of Fame Friend of the Arts Award | | Trinidad & Tobago | Yes | 2018 |
| Edwin “Crazy” Ayoung | The Performing Arts – Calypso Music | SUNSHINE Awards Hall of Fame | | Trinidad & Tobago | Yes | 2018 |
| Kenrick Thomas | The Performing Arts – Steelband Music | SUNSHINE Awards Hall of Fame | | Trinidad & Tobago | Yes | 2018 |
| Ron Berridge | The Performing Arts | SUNSHINE Awards Hall of Fame | | Trinidad & Tobago | Yes | 2018 |
| Stephen Charles | SUNSHINE Awards Corporate Award | SUNSHINE Awards Corporate Award | | Grenada | Yes | 2018 |
| Andre Alexander | Photography | Photography | | Trinidad & Tobago | Yes | 2018 |
| Karl Rodney | Contribution to Journalism | Journalism | | Jamaica | Yes | 2018 |
| Hugh Riley | Contribution to Caribbean Tourism | Contribution to Caribbean Tourism | | Barbados | Yes | 2018 |
| David Rudder | Male Vocalist of the Year | Artist | Calypso Music | Trinidad & Tobago | Yes | 1989 |
| David Rudder | Best Calypso of the Year | Artist | Calypso Music | Trinidad & Tobago | No | 1989 |
| Gregory Ballantyne | Best Upcoming Male Artists | Artist | Calypso King | Trinidad & Tobago | No | 1989 |
| Duke | Best Social Commentary | Artist | Apartheid | Trinidad & Tobago | No | 1989 |
| Funny | Best Political Commentary | Artist | Ah Soul Man | Trinidad & Tobago | No | 1989 |
| Funny | Best Creative Humor | Artist | Ah Soul Man | Trinidad & Tobago | Yes | 1989 |
| Youssouf Koumbassa | Performing Arts | African Dance | | Guinea | | |
| Professor Dr. Gordon Rohlehr | The Dom Basil Matthews SUNSHINE Award | Research | | | | |
| Father Richard Ho Lung | The Nelson Mandela Human Rights Achievement SUNSHINE Award | Humanity | | Jamaica | | |
| Yacouba Sissoko | Performing Arts | African Music | | Mali | | |
| Kirani James | SUNSHINE Award | Sports | | Grenada | | |
| Sir Garfield Sobers | SUNSHINE Award | Sports – Cricket | | Barbados | | |
| Dr Hollis Chalkdust “Liverpool | Education | | | | | |
| Alfred Mayer | SUNSHINE Awards Hall of Fame | A steelband pioneer of the 1940s | | Trinidad & Tobago | Yes | |
| Abdoulaye Diabate | Contribution to Performing Arts | African Music | | Mali | | |
| Dr. Camille Wardrop Alleyne | Contribution to Education | | | | | |
| Rupert Philo (King Swallow) | The SUNSHINE Awards Hall of Fame(TM) | Calypso Music | | Antigua & Barbuda | Yes | |
| Duke | Best Creative Humor | Artist | How Many More | Trinidad & Tobago | No | 1989 |
| Duke | Best Political Commentary | Artist | How Many More | Trinidad & Tobago | Yes | 1989 |
| DeFosto | Best Supporting Artists – Background Vocalists | Artist | I Am In Love With You | Trinidad & Tobago | No | 1989 |
| George Victory | Best Supporting Artists – Background Vocalists | Artist | Happy Music | Trinidad & Tobago | No | 1989 |
| Shandeleer | Best Party Calypso | Artist | Happy | Trinidad & Tobago | No | 1989 |
| Ronnie McIntosh | Best Upcoming Male Artists | Artist | Happy | Trinidad & Tobago | No | 1989 |
| Ronnie McIntosh | Male Vocalist of the Year | Artist | Happy | Trinidad & Tobago | No | 1989 |
| Lady Venus | Best Upcoming Female Artists | Artist | Free Up – | Trinidad & Tobago | Yes | 1989 |
| Lady Venus | Female Vocalist of the Year | Artist | Free Up – | Trinidad & Tobago | No | 1989 |
| Swallow | Best Party Calypso | Artist | Fire In The Back Seat | Antigua | Yes | 1989 |
| Swallow | Best Engineered Recording | Engineer | Fire In The Back Seat | Antigua | Yes | 1989 |
| Swallow | Best Calypso of the Year | Artist | Fire In The Back Seat | Antigua | Yes | 1989 |
| Swallow | Arranger of the Year | Arranger | Fire In The Back Seat | Antigua | No | 1989 |
| Swallow | Best Record Cover Design | Artist | Don | Antigua | No | 1989 |
| Tobago Cruso | Best Social Commentary | Artist | Don | Trinidad & Tobago | Yes | 1989 |
| Lady Wonder | Best Upcoming Female Artists | Artist | Eight Wonders of the World | Trinidad & Tobago | No | 1989 |
| Tambu | Best Calypso of the Year | Artist | Culture | Trinidad & Tobago | No | 1989 |
| Trini | Best Engineered Recording | Engineer | Cathy Ann | Trinidad & Tobago | No | 1989 |
| Gregory Ballantyne | Arranger of the Year | Arranger | Calypso Rising | Trinidad & Tobago | No | 1989 |
| David Rudder | Producer of the Year | Producer | Calypso Music | Trinidad & Tobago | No | 1989 |
| Sound Revolution | Producer of the Year | Producer | Shake It | Trinidad & Tobago | No | 1989 |
| Carl & Carol Jacobs | Producer of the Year | Producer | Savage | Trinidad & Tobago | No | 1989 |
| Carl & Carol Jacobs | Best Supporting Artists – Background Vocalists | Artist | Savage | Trinidad & Tobago | Yes | 1989 |
| Carl & Carol Jacobs | Best Engineered Recording | Engineer | Savage | Trinidad & Tobago | No | 1989 |
| Trini | Best Record Cover Design | Artist | Sailing | Trinidad & Tobago | No | 1989 |
| Trini | Best Social Commentary | Artist | Sailing | Trinidad & Tobago | No | 1989 |
| King Austin | Best Social Commentary | Artist | Progress | Trinidad & Tobago | No | 1989 |
| Natasha Wilson | Female Vocalist of the Year | Artist | One Day | Trinidad & Tobago | No | 1989 |
| Johnny King | Best Social Commentary | Artist | Nature | Trinidad & Tobago | No | 1989 |
| Mighty Arrow | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Montserrat | Yes | 1989 |
| Calypso Rose | Best Party Calypso | Artist | Leh We Punta | Trinidad & Tobago | No | 1989 |
| Calypso Rose | Female Vocalist of the Year | Artist | Leh We Punta | Trinidad & Tobago | Yes | 1989 |
| Designer | Best Engineered Recording | Engineer | Jump With Me | Trinidad & Tobago | No | 1989 |
| Designer | Male Vocalist of the Year | Artist | Jump With Me | Trinidad & Tobago | No | 1989 |
| Mighty Miller | Best Upcoming Male Artists | Artist | Jump Like An African | St. Croix USVI | No | 1989 |
| Natasha Wilson | Best Record Cover Design | Artist | Introducing Natasha Wilson | Trinidad & Tobago | No | 1989 |
| Natasha Wilson | Best Upcoming Female Artists | Artist | Introducing Natasha Wilson | Trinidad & Tobago | No | 1989 |
| George Victory | Arranger of the Year | Arranger | Hoity Toity | Trinidad & Tobago | Yes | 1989 |
| George Victory | Best Upcoming Male Artists | Artist | Hoity Toity | Trinidad & Tobago | Yes | 1989 |
| George Victory | Producer of the Year | Producer | Hoity Toity | Trinidad & Tobago | Yes | 1989 |
| Ken Philmore | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1989 |
| Merle Albino Decauteau | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1989 |
| Rudolph Charles | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1989 |
| Machel Montano | Best Record Cover Design | Artist | Too Young To Soca | Trinidad & Tobago | Yes | 1989 |
| Bumba | Best Social Commentary | Artist | They Want To Know | Barbados | No | 1989 |
| Chalkdust | Best Creative Humor | Artist | Three Blind Mice | Trinidad & Tobago | No | 1989 |
| Chalkdust | Best Political Commentary | Artist | Three Blind Mice | Trinidad & Tobago | No | 1989 |
| Short Pants | Best Political Commentary | Artist | The Law Is An Ass | Trinidad & Tobago | No | 1989 |
| Short Pants | Best Social Commentary | Artist | The Law Is An Ass | Trinidad & Tobago | No | 1989 |
| Short Pants | Best Creative Humor | Artist | The Law Is An Ass | Trinidad & Tobago | No | 1989 |
| David Rudder | Arranger of the Year | Arranger | The Hammer | Trinidad & Tobago | | 1989 |
| Lady B (Beulah Bobb) | Female Vocalist of the Year | Artist | Tell Me | Trinidad & Tobago | No | 1989 |
| DeFosto | Arranger of the Year | Arranger | Sound of Steel | Trinidad & Tobago | No | 1989 |
| Bally | Best Creative Humor | Artist | Skaka Shaka | Trinidad & Tobago | No | 1989 |
| Bally | Best Political Commentary | Artist | Shaka Shaka | Trinidad & Tobago | No | 1989 |
| Sound Revolution | Best Party Calypso | Artist | Shake It | Trinidad & Tobago | No | 1989 |
| Sound Revolution | Best Supporting Artists – Background Vocalists | Artist | Shake It | Trinidad & Tobago | No | 1989 |
| Sound Revolution | Male Vocalist of the Year | Artist | Shake It | Trinidad & Tobago | No | 1989 |
| Calypso Rose | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1989 |
| Desperadoes Steel Orchestra | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1989 |
| Johnny King | Best Party Calypso | Artist | Wet Meh Down | Trinidad & Tobago | No | 1989 |
| Johnny King | Best Engineered Recording | Engineer | Wet Meh Down | Trinidad & Tobago | No | 1989 |
| Johnny King | Best Calypso of the Year | Artist | Wet Meh Down | Trinidad & Tobago | No | 1989 |
| Ralph McDonald | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | United States | Yes | 1989 |
| Trinidad All Steel Percussions Orchestra (TASPO) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1989 |
| George Goddard | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1989 |
| Ellie Manette | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1989 |
| Lord Pretender (Alric Farrell) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1989 |
| Neville Jules | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1989 |
| Winston Spree | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1989 |
| Lord Kitchener (Aldwin Roberts) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1989 |
| Lord Executor (Phillip Garcia) | The SUNSHINE Awards Hall of Fame(TM) | Inductee For Calypso Music | | Trinidad & Tobago | Yes | 1989 |
| Walter Chieftain Douglas | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1989 |
| Atilla the Hun (Raymond Quevado) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1989 |
| Mighty Sparrow | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1989 |
| Othello Molino | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1989 |
| Pat Bishop | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1989 |
| Robert Greenidge | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1989 |
| Amoco Renegades | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1989 |
| Boggsie Sharpe | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1989 |
| Granville Straker | Producer of the Year | Producer | Carnival Is The Answer / Chalkdust | St. Vincent and the Grenadines | No | 1990 |
| Lady M | Best New Female Vocalist | Artist | Can | USVI | No | 1990 |
| Black Stalin | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso Peoples Choice | Trinidad & Tobago | Yes | 1990 |
| Raft Robertson | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso Jazz | Trinidad & Tobago | Yes | 1990 |
| Toby Tobas | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso Jazz | Trinidad & Tobago | Yes | 1990 |
| Joe Brown | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso Jazz | Trinidad & Tobago | Yes | 1990 |
| Clive Zander | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso Jazz | Trinidad & Tobago | Yes | 1990 |
| Earl Rodney | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso Jazz | Trinidad & Tobago | Yes | 1990 |
| Paul Bill Trotman | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso | Trinidad & Tobago | Yes | 1990 |
| Anthony | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso | Barbados | Yes | 1990 |
| Kathleen | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso | Trinidad & Tobago | Yes | 1990 |
| Lord Nelson / Byron Lee | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso | Trinidad & Tobago / Jamaica | Yes | 1990 |
| Aldwin | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso | Trinidad & Tobago | Yes | 1990 |
| Frank Vialva | Producer of the Year | Producer | Ah Cyar Wine / Delamo | | No | 1990 |
| Linc | Best New Male Artist | Artist | Ah Don | | No | 1990 |
| Natasha Wilson | Female Vocalist of the Year | Artist | A Vex For Dat | Trinidad & Tobago | No | 1990 |
| Dave Samuels | Best Record Cover Design | Artist | Woy | Antigua | No | 1989 |
| Denyse Plummer | Female Vocalist of the Year | Artist | Woman Is Boss | Trinidad & Tobago | No | 1989 |
| Johnny King | Best Supporting Artists – Background Vocalists | Artist | Wet Meh Down | Trinidad & Tobago | No | 1989 |
| Johnny King | Producer of the Year | Producer | Wet Meh Down | Trinidad & Tobago | No | 1989 |
| Leston Paul | Arranger of the Year | Arranger | Pantastic | Trinidad & Tobago | No | 1990 |
| Lady Wonder | Female Vocalist of the Year | Artist | Pantastic | Trinidad & Tobago | No | 1990 |
| King Austin | Male Vocalist of the Year | Artist | Oyoyoye | Trinidad & Tobago | No | 1990 |
| King Austin | Best Creative Humor | Artist | Oyoyoye | Trinidad & Tobago | No | 1990 |
| Charlo Charles | Best New Male Artist | Artist | Mas In Winnipeg | | No | 1990 |
| Bally | Best Creative Humor | Artist | Maxi Dub | Trinidad & Tobago | No | 1990 |
| Lovey | Female Vocalist of the Year | Artist | Leh Go Meh Hand | Trinidad & Tobago | No | 1990 |
| Jerome Francois | Best Engineered Recording | Engineer | Leh We Slow Down / Contender | | No | 1990 |
| King Socrates | Best Social Commentary | Artist | Killer In The Road | USVI | No | 1990 |
| King Socrates | Best Calypso of the Year | Artist | Killer In The Road | USVI | No | 1990 |
| Lovey | Best New Female Vocalist | Artist | Leh Go Meh Hand | Trinidad & Tobago | No | 1990 |
| Lady Beast | Best New Female Vocalist | Artist | Junior Calypso Criticism | USVI | No | 1990 |
| Lady Venus | Female Vocalist of the Year | Artist | Jam It Deh | Trinidad & Tobago | No | 1990 |
| Allrounder | Best Creative Humor | Artist | Innocent Jimmy | Trinidad & Tobago | No | 1990 |
| Errol Sookraj | Best Engineered Recording | Engineer | Innocent Jimmy / Allrounder | | No | 1990 |
| Wizard | Best Calypso of the Year | Artist | IMF | Trinidad & Tobago | No | 1990 |
| Wizard | Best Political Commentary | Artist | IMF | Grenada | No | 1990 |
| Errol Ince | Producer of the Year | Producer | Errol Ince & Friends | Trinidad & Tobago | No | 1990 |
| Singing Dianne | Best Supporting Artists – Background Vocalists | Artist | Errol Ince & Friends | | No | 1990 |
| Glenda Ifill | Best Supporting Artists – Background Vocalists | Artist | Errol Ince & Friends | | No | 1990 |
| Lovey | Best Supporting Artists – Background Vocalists | Artist | Errol Ince & Friends | | No | 1990 |
| Poser | Best Supporting Artists – Background Vocalists | Artist | Errol Ince & Friends | | No | 1990 |
| Randy Phipps | Best Engineered Recording | Engineer | Errol Ince & Friends | | No | 1990 |
| John Evans | Best Engineered Recording | Engineer | Errol Ince & Friends | | No | 1990 |
| Errol Ince | Arranger of the Year | Arranger | Errol Ince & Friends | Trinidad & Tobago | No | 1990 |
| George Victory | Best Supporting Artists – Background Vocalists | Artist | Errol Ince & Friends | | No | 1990 |
| E. Bianca | Best Supporting Artists – Background Vocalists | Artist | Errol Ince & Friends | | No | 1990 |
| Designer | Best Supporting Artists – Background Vocalists | Artist | Errol Ince & Friends | | No | 1990 |
| Baron | Best Supporting Artists – Background Vocalists | Artist | Errol Ince & Friends | | No | 1990 |
| Lenox Picou | Best Supporting Artists – Background Vocalists | Artist | Congo Man / Sparrow | | No | 1990 |
| Renske Farrel | Best Supporting Artists – Background Vocalists | Artist | Congo Man / Sparrow | | No | 1990 |
| Janet Alleyne | Best Supporting Artists – Background Vocalists | Artist | Congo Man / Sparrow | | No | 1990 |
| Glenda Ifill | Best Supporting Artists – Background Vocalists | Artist | Congo Man / Sparrow | | No | 1990 |
| George Victory | Best Supporting Artists – Background Vocalists | Artist | Congo Man / Sparrow | | No | 1990 |
| Designer | Best Supporting Artists – Background Vocalists | Artist | Congo Man / Sparrow | | No | 1990 |
| Sparrow | Male Vocalist of the Year | Artist | Congo Man | Trinidad & Tobago | No | 1990 |
| Sparrow | Best Calypso of the Year | Artist | Congo Man | Trinidad & Tobago | No | 1990 |
| Lady Bones | Best New Female Vocalist | Artist | Channel 3 | USVI | No | 1990 |
| Chalkdust | Best Social Commentary | Artist | Carnival Is The Answer | Trinidad & Tobago | No | 1990 |
| Chalkdust | Best Political Commentary | Artist | Carnival Is The Answer | Trinidad & Tobago | No | 1990 |
| Anthony Prospect | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Steelband | Trinidad & Tobago | Yes | 1990 |
| Amoco Renegades | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Steelband | Trinidad & Tobago | Yes | 1990 |
| Kenny J | Male Vocalist of the Year | Artist | Slow Down | Trinidad & Tobago | No | 1990 |
| Kenny J. | Best Social Commentary | Artist | Slow Down | Trinidad & Tobago | No | 1990 |
| Kenny J. | Best Calypso of the Year | Artist | Slow Down | Trinidad & Tobago | No | 1990 |
| Kenny J | Best New Male Artist | Artist | Slow Down | | No | 1990 |
| Soca Prince | Best New Male Artist | Artist | Shelly | | No | 1990 |
| Soca Prince | Male Vocalist of the Year | Artist | Shelly | Trinidad & Tobago | No | 1990 |
| Jude Bethell | Arranger of the Year | Arranger | Shelly / Soca Prince | Trinidad & Tobago | No | 1990 |
| Janet Alleyne | Best Supporting Artists – Background Vocalists | Artist | Shelly / Soca Prince | | No | 1990 |
| Marcia McClean | Best Supporting Artists – Background Vocalists | Artist | Shelly / Soca Prince | | No | 1990 |
| Margrer Stevens | Best Supporting Artists – Background Vocalists | Artist | Shelly / Soca Prince | | No | 1990 |
| Emmanuel Ector | Arranger of the Year | Arranger | Shakin It / Shandeleer | Trinidad & Tobago | No | 1990 |
| Shandeleer | Best Supporting Artists – Background Vocalists | Artist | Shakin It / Shandeleer | | No | 1990 |
| Wayne Kirton | Arranger of the Year | Arranger | Save the Last Dance / Mingo | Trinidad & Tobago | No | 1990 |
| King Derby | Best Political Commentary | Artist | Rum & Coke Gang | Antigua | No | 1990 |
| Prince Pierre | Best New Male Artist | Artist | Rumba To The Soca | | No | 1990 |
| Shabaka | Best Supporting Artists – Background Vocalists | Artist | Power of Soca / Shabaka | | No | 1990 |
| Elizabeth Garib | Best Supporting Artists – Background Vocalists | Artist | Power of Soca / Shabaka | | No | 1990 |
| Janice Edwards | Best Supporting Artists – Background Vocalists | Artist | Power of Soca / Shabaka | | No | 1990 |
| Kenny Phillips | Best Engineered Recording | Engineer | Watch Out My Children / Shorty I | | No | 1990 |
| Tony Benjaman | Best Engineered Recording | Engineer | Watch Out My Children / Shorty I | | No | 1990 |
| Ras Shorty I | Best Social Commentary | Artist | Watch Out My Children | Trinidad & Tobago | No | 1990 |
| Lord Nelson | Best Political Commentary | Artist | Warning | Trinidad & Tobago | No | 1990 |
| Lord Beginner (Egbert Moore) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1990 |
| Growling Tiger (Neville Macano) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1990 |
| Arthur DeCoteau | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1990 |
| Patsy Haynes | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1990 |
| The Mighty Sparrow (Dr. Slinger Francisco) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1990 |
| Denyse Plummer | Best Social Commentary | Artist | Together Right Here | Trinidad & Tobago | No | 1990 |
| Denyse Plummer | Female Vocalist of the Year | Artist | Together Right Here | Trinidad & Tobago | No | 1990 |
| Original Defosto | Best Creative Humor | Artist | Tolum Boom Boom | Trinidad & Tobago | No | 1990 |
| Carl & Carol Jacobs | Producer of the Year | Producer | Street Dancing / Carl & Carol | Trinidad & Tobago | No | 1990 |
| Carl Jacobs | Male Vocalist of the Year | Artist | Street Dancing | Trinidad & Tobago | No | 1990 |
| VAT 19 Fonclare | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Steelband | Trinidad & Tobago | Yes | 1990 |
| Raymond Shaw | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Steelband | Trinidad & Tobago | Yes | 1990 |
| Kim Loy-Wong | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Steelband | Trinidad & Tobago | Yes | 1990 |
| Kelvin Scoon | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Steelband | Trinidad & Tobago | Yes | 1990 |
| Invaders Engine Room | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Steelband | Trinidad & Tobago | Yes | 1990 |
| Joycelyn Pierre | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Steelband | Trinidad & Tobago | Yes | 1990 |
| Ronnie McIntosh | Male Vocalist of the Year | Artist | Jump and Breakaway | Trinidad & Tobago | No | 1991 |
| Joe Brown | Producer of the Year | Producer | Jump and Breakaway | Trinidad & Tobago | Yes | 1991 |
| Lady Venus | Female Vocalist of the Year | Artist | It Burning Me | Trinidad & Tobago | No | 1991 |
| Leston Paul | Arranger of the Year | Arranger | Get Up and Dance | Trinidad & Tobago | Yes | 1991 |
| David English / Jon Evans | Best Engineered Recording | Engineer | Get Up and Dance | Trinidad & Tobago | Yes | 1991 |
| Leston Paul | Best Party Calypso | Artist | Get Up and Dance | Trinidad & Tobago | No | 1991 |
| Lady Pearl | Female Vocalist of the Year | Artist | Daughter Talk To Me | Canada | No | 1991 |
| Lenox Picou | Best New Male Artist | Artist | Doh Bother Meh | Trinidad & Tobago | Yes | 1991 |
| Leston Paul | Best Party Calypso | Artist | Doh Bother Meh | Trinidad & Tobago | No | 1991 |
| Lenox Picou | Male Vocalist of the Year | Artist | Doh Bother Meh | Trinidad & Tobago | No | 1991 |
| Cornell Phillip / WCK | Best Engineered Recording | Engineer | Culture Shock | Dominica | No | 1991 |
| Fitzgerald | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Calypso Music | Trinidad & Tobago | Yes | 1991 |
| Kenny J | Producer of the Year | Producer | Addicted To Sweet Soca | Trinidad & Tobago | No | 1991 |
| Kenny J | Male Vocalist of the Year | Artist | Addicted To Sweet Soca | Trinidad & Tobago | No | 1991 |
| Kenny J | Best Party Calypso | Artist | Addicted To Sweet Soca | Trinidad & Tobago | No | 1991 |
| Burning Flames | Best Creative Humor | Artist | Workey Workey | Trinidad & Tobago | No | 1990 |
| Lady Pearl | Best Political Commentary | Artist | Winnie Mandella | Canada | No | 1990 |
| Lady Pearl | Best New Female Vocalist | Artist | Winnie Mandella | Canada | No | 1990 |
| Ras Shorty I | Best Calypso of the Year | Artist | Watch Out My Children | Trinidad & Tobago | No | 1990 |
| Ras Shorty I | Producer of the Year | Producer | Watch Out My Children | Trinidad & Tobago | No | 1990 |
| Baron | Best Calypso of the Year | Artist | Soca Pan Tuner | Trinidad & Tobago | No | 1991 |
| Luta | Best Social Commentary | Artist | Soca For Me | Trinidad & Tobago | No | 1991 |
| Sugar Aloes | Best Social Commentary | Artist | Sign of the End of Time | Trinidad & Tobago | Yes | 1991 |
| Sugar Aloes | Best Calypso of the Year | Artist | Sign of the End of Time | Trinidad & Tobago | No | 1991 |
| Machel Montano | Best Social Commentary | Artist | Say No To Dope | Trinidad & Tobago | No | 1991 |
| WCK Band | Arranger of the Year | Arranger | Rock Steady | Dominica | No | 1991 |
| Terror | Best Social Commentary | Artist | Panman Jammimg Pan | Trinidad & Tobago | No | 1991 |
| Designer | Best Party Calypso | Artist | Pan by Storm | Trinidad & Tobago | No | 1991 |
| Designer | Male Vocalist of the Year | Artist | Pan By Storm | Trinidad & Tobago | Yes | 1991 |
| George Victory | Arranger of the Year | Arranger | Pan by Storm | Trinidad & Tobago | No | 1991 |
| Designer | Best Calypso of the Year | Artist | Pan by Storm | Trinidad & Tobago | No | 1991 |
| Kevin Anthony / Jon Evans | Best Engineered Recording | Engineer | Pan By Storm | Trinidad & Tobago | No | 1991 |
| Jason | Best Political Commentary | Artist | Overcome | Canada | No | 1991 |
| Mighty Potter | Best Political Commentary | Artist | Minority | USVI | No | 1991 |
| Prince Pierre | Producer of the Year | Producer | Lombada Locomotion | Trinidad & Tobago | No | 1991 |
| Sugar Caines | Best New Male Artist | Artist | Make a Change | Grenada | No | 1991 |
| Nelson | Best Calypso of the Year | Artist | Keys to the City | Trinidad & Tobago | No | 1991 |
| Emmanuel Ector | Arranger of the Year | Arranger | Jump and Breakaway | Trinidad & Tobago | No | 1991 |
| Shandileer | Best Calypso of the Year | Artist | Jump and Breakaway | Trinidad & Tobago | Yes | 1991 |
| Shaandileer | Best Party Calypso | Artist | Jump and Breakaway | Trinidad & Tobago | Yes | 1991 |
| Jon Evans | Best Engineered Recording | Engineer | Alantik | Trinidad & Tobago | No | 1992 |
| Preacher | Best Political Commentary | Artist | Abu Baka Take Over | Trinidad & Tobago | No | 1992 |
| Bindley B. | Best New Male Artist | Artist | Wounded Soldier | Grenada | No | 1991 |
| King Progress | Best Political Commentary | Artist | Turning Point | Antigua | No | 1991 |
| Andrew Labastide | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1991 |
| Joe Crick | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1991 |
| Roaring Lion | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1991 |
| Roaring Lion | 1998 Journalist Award | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1991 |
| Houdini | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1991 |
| Alexander Ragtime Band | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1991 |
| Prince Unique | Best New Male Artist | Artist | Tobago Wil Rise | Trinidad & Tobago | No | 1991 |
| Denyse Plummer | Female Vocalist of the Year | Artist | The Message | Trinidad & Tobago | No | 1991 |
| Sugar Aloes | Best Political Commentary | Artist | The Judge | Trinidad & Tobago | Yes | 1991 |
| Frankie McIntosh | Arranger of the Year | Arranger | The Jacket | St. Vincent and the Grenadines | No | 1991 |
| Natasha | Best Calypso of the Year | Artist | Sweet T & T | Trinidad & Tobago | No | 1991 |
| Natasha Wilson | Best Social Commentary | Artist | Sweet T & T | Trinidad & Tobago | No | 1991 |
| Natasha Wilson | Female Vocalist of the Year | Artist | Sweet T & T | Trinidad & Tobago | Yes | 1991 |
| Leston Paul | Producer of the Year | Producer | Sweetie Pie | Trinidad & Tobago | No | 1991 |
| Desperadoes Steel Orchestra Bertie Marshall | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | Steelband | Trinidad & Tobago | Yes | 1991 |
| Baron | Best Party Calypso | Artist | Soca Pan Tuner | Trinidad & Tobago | No | 1991 |
| David Rudder & Wayne Bruno | Arranger of the Year | Arranger | Nuff Respect | Trinidad & Tobago | No | 1992 |
| Shirlane Hendrickson | Female Vocalist of the Year | Artist | My Opinion | Trinidad & Tobago | No | 1992 |
| Frankie McIntosh | Arranger of the Year | Arranger | Looters | St. Vincent and the Grenadines | No | 1992 |
| Sugar Caines | Best Social Commentary | Artist | Looters | Trinidad & Tobago | No | 1992 |
| Errol Sookraj | Best Engineered Recording | Engineer | Melody Sweet | Trinidad & Tobago | Yes | 1992 |
| Devon George | Best Party Calypso | Artist | If Ah Rude Ah Rude | Trinidad & Tobago | No | 1992 |
| David Rudder | Best Calypso of the Year | Artist | Hoosay | Trinidad & Tobago | Yes | 1992 |
| David Rudder | Best Social Commentary | Artist | Hoosay | Trinidad & Tobago | Yes | 1992 |
| King Progress | Best Political Commentary | Artist | Heaven Help Us | Antigua | Yes | 1992 |
| Super Blue | Best Party Calypso | Artist | Get Something And Wave | Trinidad & Tobago | No | 1992 |
| Rootsman | Best Political Commentary | Artist | Good Morning Mr. Manning | Trinidad & Tobago | No | 1992 |
| Poser | Best Social Commentary | Artist | Frustration | Trinidad & Tobago | No | 1992 |
| Lady Wonder | Best Creative Humor | Artist | Funny Football Terms | Trinidad & Tobago | No | 1992 |
| Pelham Goddard | Arranger of the Year | Arranger | Get Something And Wave | Trinidad & Tobago | Yes | 1992 |
| Super Blue | Best Calypso of the Year | Artist | Get Something And Wave | Trinidad & Tobago | No | 1992 |
| Lenox Picou | Male Vocalist of the Year | Artist | Fire In The Area | Trinidad & Tobago | No | 1992 |
| Ed Watson | Producer of the Year | Producer | Everybody | Trinidad & Tobago | No | 1992 |
| Colin Lucas | Best Party Calypso | Artist | Dollar | Trinidad & Tobago | Yes | 1992 |
| Kenny J | Male Vocalist of the Year | Artist | Drug Abuse Is Destructive | Trinidad & Tobago | No | 1992 |
| Kenny J | Producer of the Year | Producer | Drug Abuse Is Destructive | Trinidad & Tobago | No | 1992 |
| Colin Lucas | Best New Male Artist | Artist | Dollar | Trinidad & Tobago | Yes | 1992 |
| Natasha Wilson | Best Social Commentary | Artist | Demons In T & T | Trinidad & Tobago | No | 1992 |
| Natasha Wilson | Female Vocalist of the Year | Artist | Demons in T & T | Trinidad & Tobago | Yes | 1992 |
| Errol Ince | Producer of the Year | Producer | Demons in T & T | Trinidad & Tobago | Yes | 1992 |
| Julien Browne | Best Engineered Recording | Engineer | Do Me As You Like | Trinidad & Tobago | No | 1992 |
| Joe Brown | Producer of the Year | Producer | Do What you Want | Trinidad & Tobago | No | 1992 |
| Colin Lucas | Best Calypso of the Year | Artist | Dollar | Trinidad & Tobago | No | 1992 |
| Colin Lucas | Best Creative Humor | Artist | Dollar | Trinidad & Tobago | Yes | 1992 |
| Randy Isaac | Best New Male Artist | Artist | Crack Pipe | Grenada | No | 1992 |
| Bindley B | Best New Male Artist | Artist | Cloudy Horizons | Grenada | No | 1992 |
| Denyse Plummer | Female Vocalist of the Year | Artist | Carnival Killer | Trinidad & Tobago | No | 1992 |
| Sugar Aloes | Male Vocalist of the Year | Artist | Carnival Fever | Trinidad & Tobago | No | 1992 |
| X-Press Band | Best Supporting Artists – Background Vocalists | Artist | Can Find Meh Woman | USVI | Yes | 1992 |
| X-Press Band | Best Party Calypso | Artist | Can Find Meh Woman | USVI | No | 1992 |
| Al Baptiste | Arranger of the Year | Arranger | Can | Trinidad & Tobago | No | 1992 |
| David Rudder | Male Vocalist of the Year | Artist | Calypso Rising | Trinidad & Tobago | Yes | 1992 |
| Designer | Male Vocalist of the Year | Artist | Calypso | Trinidad & Tobago | No | 1992 |
| Prince Unique | Best New Male Artist | Artist | Be A Believer | Trinidad & Tobago | No | 1992 |
| Poser | Best Creative Humor | Artist | Bad Pronounciation | Trinidad & Tobago | No | 1992 |
| Trini | Best Political Commentary | Artist | Animal Farm | Trinidad & Tobago | No | 1992 |
| Mighty Spoiler (Theophilus Phillip) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1992 |
| King Radio (Norman Spann) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1992 |
| Chinee Patrick (Patrick Jones) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1992 |
| Andre Tanker | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1992 |
| Dr. Hollis Chalkdust Liverpool | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Recipient | | Trinidad & Tobago | Yes | 1992 |
| Leston Paul | Arranger of the Year | Arranger | This Melody Sweet | Trinidad & Tobago | No | 1992 |
| Baron | Best Calypso of the Year | Artist | This Melody Sweet | Trinidad & Tobago | No | 1992 |
| Baron | Best Party Calypso | Artist | This Melody Sweet | Trinidad & Tobago | No | 1992 |
| Poody | Best Creative Humor | Artist | Tickle | Trinidad & Tobago | No | 1992 |
| Xtatik | Best Supporting Artists – Background Vocalists | Artist | Take Me Back | Trinidad & Tobago | No | 1992 |
| Machel Montano | Male Vocalist of the Year | Artist | Take Me Back | Trinidad & Tobago | No | 1992 |
| Shandileer | Best Social Commentary | Artist | South Africa Will Rise | Trinidad & Tobago | No | 1992 |
| Weldon Wallace | Best Supporting Artists – Background Vocalists | Artist | Soldiers We Are All | Barbados | No | 1992 |
| Romeo | Best Supporting Artists – Background Vocalists | Artist | Soldiers We Are All | Barbados | No | 1992 |
| Lisa & Lorie | Best Supporting Artists – Background Vocalists | Artist | Soldiers We Are All | Barbados | No | 1992 |
| Randy Isaac | Best Political Commentary | Artist | Selfish Pride | Grenada | No | 1992 |
| Randy Isaac | Best Creative Humor | Artist | Red Light | Grenada | No | 1992 |
| Cro Cro | Best Social Commentary | Artist | Race to Monarchy | Trinidad & Tobago | No | 1992 |
| Russell Codagan | Best New Male Artist | Artist | Party Mash Up | Trinidad & Tobago | No | 1992 |
| Venus | Female Vocalist of the Year | Artist | Once Upon A Time | Trinidad & Tobago | No | 1992 |
| Colin Lucas | Producer of the Year | Producer | Doh Wine | Trinidad & Tobago | No | 1993 |
| Stalin | Best Political Commentary | Artist | Cry Of The Caribbean | Trinidad & Tobago | No | 1993 |
| Stalin | Best Party Calypso | Artist | Come With It | Trinidad & Tobago | No | 1993 |
| Marcia Miranda | Best New Female Vocalist | Artist | Children Rise | Trinidad & Tobago | No | 1993 |
| Frankie McIntosh | Arranger of the Year | Arranger | Caribbean Party | St. Vincent and the Grenadines | No | 1993 |
| Shirlane Hendrickson | Best Creative Humor | Artist | Bigwood ’91 | Trinidad & Tobago | No | 1993 |
| United Sisters | Best New Female Vocalist | Artist | Ambataila Woman | Trinidad & Tobago | No | 1993 |
| Chalkdust | Best Political Commentary | Artist | You the Jury | Trinidad & Tobago | No | 1992 |
| Prince Unique | Best Party Calypso | Artist | Wine Yur Waist | Trinidad & Tobago | No | 1992 |
| Charlo Charles | Producer of the Year | Producer | Wine Yur Waist | Trinidad & Tobago | No | 1992 |
| Shandileer | Best Calypso of the Year | Artist | We Pushin | Trinidad & Tobago | No | 1992 |
| Anthony Williams | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1992 |
| Frankie Francis | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1992 |
| Lord and Lady Iere | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1992 |
| Super Blue | Best Party Calypso | Artist | Jab Jab | Trinidad & Tobago | Yes | 1993 |
| Super Blue | Producer of the Year | Producer | Jab Jab | Trinidad & Tobago | No | 1993 |
| Shadow | Best Social Commentary | Artist | Hard Head | Trinidad & Tobago | No | 1993 |
| Explainer | Best Social Commentary | Artist | Fast Lane | Trinidad & Tobago | No | 1993 |
| Crazy | Best Calypso of the Year | Artist | De Party Now Start | Trinidad & Tobago | No | 1993 |
| Colin Lucas | Best Party Calypso | Artist | Doh Wine | Trinidad & Tobago | No | 1993 |
| Julien Williams | Producer of the Year | Producer | Panelope | Trinidad & Tobago | No | 1993 |
| Crazy | Male Vocalist of the Year | Artist | Panelope | Trinidad & Tobago | No | 1993 |
| Robert Greenidge | Best Party Calypso | Artist | Pan Is Meh Jumbie | Trinidad & Tobago | No | 1993 |
| Joe Brown | Producer of the Year | Producer | Pan Is Meh Jumbie | Trinidad & Tobago | No | 1993 |
| Baron | Male Vocalist of the Year | Artist | One For The Road | Trinidad & Tobago | Yes | 1993 |
| Leston Paul | Arranger of the Year | Arranger | One For The Road | Trinidad & Tobago | No | 1993 |
| Baron | Best Calypso of the Year | Artist | One For The Road | Trinidad & Tobago | No | 1993 |
| Trinidad Rio | Best Creative Humor | Artist | No Drawers | Trinidad & Tobago | Yes | 1993 |
| Rapso Riddum Band | Best Political Commentary | Artist | Never Surrender | Trinidad & Tobago | No | 1993 |
| Atlantik | Best Party Calypso | Artist | Music To Dance | Trinidad & Tobago | No | 1993 |
| Shadow | Best Calypso of the Year | Artist | Music | Trinidad & Tobago | No | 1993 |
| Robert Greenidge | Best Social Commentary | Artist | Man Konk Out | Trinidad & Tobago | No | 1993 |
| Yur Happening | Best Creative Humor | Artist | Massive Chandilier | Trinidad & Tobago | No | 1993 |
| Randy Isaac | Male Vocalist of the Year | Artist | Mini Skirt | Grenada | No | 1993 |
| Luta | Best Social Commentary | Artist | Law & Justice | Trinidad & Tobago | No | 1993 |
| Second Imij | Best Party Calypso | Artist | Jump | Trinidad & Tobago | No | 1993 |
| Russell Cadogan | Male Vocalist of the Year | Artist | Jump | Trinidad & Tobago | No | 1993 |
| Second Imij | Producer of the Year | Producer | Jump | Trinidad & Tobago | Yes | 1993 |
| Second Imij | Arranger of the Year | Arranger | Jump | Trinidad & Tobago | Yes | 1993 |
| Super Blue | Best Calypso of the Year | Artist | Jab Jab | Trinidad & Tobago | Yes | 1993 |
| Clifton Mighty Bomber Ryan | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypsonian | | Trinidad & Tobago | Yes | 1993 |
| Amoco Renegades | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | 1993 Steelband Panorama Champions | | Trinidad & Tobago | Yes | 1993 |
| Junior Regrello | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Artistic Director | | Trinidad & Tobago | Yes | 1993 |
| Luta | Best Political Commentary | Artist | Think Again | Trinidad & Tobago | No | 1993 |
| Designer | Male Vocalist of the Year | Artist | This Is It | Trinidad & Tobago | No | 1993 |
| Singing Sandra | Best Calypso of the Year | Artist | The War Goes On | Trinidad & Tobago | No | 1993 |
| Singing Sandra | Best Political Commentary | Artist | The War Goes On | Trinidad & Tobago | Yes | 1993 |
| Singing Sandra | Best Social Commentary | Artist | The War Goes On | Trinidad & Tobago | Yes | 1993 |
| Singing Sandra | Female Vocalist of the Year | Artist | The War Goes On | Trinidad & Tobago | No | 1993 |
| Marcia Miranda | Female Vocalist of the Year | Artist | There’s More to Love | Trinidad & Tobago | No | 1993 |
| Granville Straker | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Record Producer | | St. Vincent and the Grenadines | Yes | 1993 |
| Cro Cro | Best Political Commentary | Artist | Sham We Doh Want It | Trinidad & Tobago | No | 1993 |
| Designer | Best Party Calypso | Artist | Rati-Ray | Trinidad & Tobago | No | 1993 |
| Julien Williams & Leston Paul | Producer of the Year | Producer | Rati-Ray | Trinidad & Tobago | No | 1993 |
| Designer | Best Calypso of the Year | Artist | Rati-Ray | Trinidad & Tobago | No | 1993 |
| Singing Sonia | Best New Female Vocalist | Artist | Professional Advice | Trinidad & Tobago | Yes | 1993 |
| Singing Sonia | Female Vocalist of the Year | Artist | Professional Advice | Trinidad & Tobago | No | 1993 |
| Chalkdust | Best Creative Humor | Artist | Qualifications Of A Politician | Trinidad & Tobago | No | 1993 |
| Singing Sonia | Best Creative Humor | Artist | Professional Advice | Trinidad & Tobago | No | 1993 |
| Sharlene Boodram | Best New Female Vocalist | Artist | Party Friend | Trinidad & Tobago | No | 1993 |
| Paul | Best Party Calypso | Artist | Crazy | Trinidad & Tobago | Yes | 1994 |
| Red Plastic Bag | Best Social Commentary | Artist | Confidence | Barbados | No | 1994 |
| Natasha | Female Vocalist of the Year | Artist | Chill Out | Trinidad & Tobago | Yes | 1994 |
| Vernon Dr. Solo Benjamin | Arranger of the Year | Arranger | Bumpa to Bumpa | Grenada | No | 1994 |
| Black Stalin | Best Social Commentary | Artist | Black Man Killing Black Man | Trinidad & Tobago | Yes | 1994 |
| Jam & Wine | Best Party Calypso | Artist | Bally | Trinidad & Tobago | No | 1994 |
| Super Blue/Eddie Grant | Producer of the Year | Producer | Bacchanal Time | Trinidad & Tobago / Barbados | No | 1994 |
| Tigress (Joanne Rowley) | Female Vocalist of the Year | Artist | Ah Wine Back on You | Trinidad & Tobago | No | 1994 |
| Singing Sonia | Best Creative Humor | Artist | Ah Man For Meh Pan | Trinidad & Tobago | No | 1994 |
| Ella Andall | Female Vocalist of the Year | Artist | Women of the Sun | Trinidad & Tobago | Yes | 1993 |
| Natasha Wilson | Female Vocalist of the Year | Artist | Unite Caribbean People | Trinidad & Tobago | No | 1993 |
| Natasha Wilson | Best Social Commentary | Artist | Unite Caribbean People | Trinidad & Tobago | No | 1993 |
| Errol Ince | Arranger of the Year | Arranger | Unite Caribbean People | Trinidad & Tobago | No | 1993 |
| Roderick Borde | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1993 |
| Chic McCrew | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1993 |
| Kelvin Hart | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1993 |
| Lord Melody | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1993 |
| Mighty Cypher | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1993 |
| Sundar Popo | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Chutnuy-Soca Artist | | Trinidad & Tobago | Yes | 1993 |
| John Agitation | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Commedian | | Trinidad & Tobago | Yes | 1993 |
| Boyie Mitchell | Arranger of the Year | Arranger | Mystery Band | Trinidad & Tobago | Yes | 1994 |
| Kitchener | Male Vocalist of the Year | Artist | Mystery Band | Trinidad & Tobago | No | 1994 |
| Flying Cloud | Best New Male Artist | Artist | Just Wine Back | Grenada | No | 1994 |
| Chalkdust | Best Social Commentary | Artist | Kaiso in the Hospital | Trinidad & Tobago | No | 1994 |
| Mystery Band | Best Calypso of the Year | Artist | Kitchener | Trinidad & Tobago | Yes | 1994 |
| Mystery Band | Best Party Calypso | Artist | Kitchener | Trinidad & Tobago | No | 1994 |
| David Rudder | Best Social Commentary | Artist | L.A. | Trinidad & Tobago | No | 1994 |
| Red Plastic Bag | Best Creative Humor | Artist | Jackass | Barbados | No | 1994 |
| Poody | Best Creative Humor | Artist | How it Hang it Swing | Trinidad & Tobago | No | 1994 |
| Sharlene Boodram | Female Vocalist of the Year | Artist | I Love Meh Nanny | Trinidad & Tobago | No | 1994 |
| Lady B (Beulah Bobb) | Female Vocalist of the Year | Artist | Heroes | Trinidad & Tobago | No | 1994 |
| King Short Shirt | Best New Male Artist | Artist | Heaven Help Mankind | Antigua | No | 1994 |
| King Short Shirt | Best Social Commentary | Artist | Heaven Help Mankind | Antigua | No | 1994 |
| Baron | Male Vocalist of the Year | Artist | Heatwave | Trinidad & Tobago | No | 1994 |
| Luta | Best Social Commentary | Artist | Hang Dem | Trinidad & Tobago | No | 1994 |
| Shirland King Fighter Wilson | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypsonian | | Guyana | Yes | 1994 |
| David Rudder | Male Vocalist of the Year | Artist | Dus In The Face | Trinidad & Tobago | No | 1994 |
| Dus’ In Deh Face | Best Calypso of the Year | Artist | David Rudder | Trinidad & Tobago | No | 1994 |
| Singing Sandra | Female Vocalist of the Year | Artist | Discipline | Trinidad & Tobago | No | 1994 |
| Paul | Best Calypso of the Year | Artist | Crazy | Trinidad & Tobago | No | 1994 |
| Vernon Dr. Solo Benjamin | Best New Male Artist | Artist | Teardrops | Grenada | No | 1994 |
| Bacchanal Time | Best Calypso of the Year | Artist | Super Blue | Trinidad & Tobago | No | 1994 |
| Bacchanal Time | Best Party Calypso | Artist | Super Blue | Trinidad & Tobago | Yes | 1994 |
| Try Again | Best Calypso of the Year | Artist | Sparrow | Trinidad & Tobago | No | 1994 |
| Wine On Ah Bumsee | Best Party Calypso | Artist | Rikki Jai | Trinidad & Tobago | No | 1994 |
| Ragga Ragga | Best Party Calypso | Artist | Red Plastic Bag | Barbados | No | 1994 |
| Luta | Best Creative Humor | Artist | Q | Trinidad & Tobago | No | 1994 |
| Nicholas Brancker | Arranger of the Year | Arranger | Ragga Ragga | Barbados | No | 1994 |
| Red Plastic Bag | Best New Male Artist | Artist | Ragga Ragga | Barbados | Yes | 1994 |
| Nicholas Brancker/Mac Fingall | Producer of the Year | Producer | Ragga Ragga | Barbados / Barbados | No | 1994 |
| David Rudder | Best Creative Humor | Artist | Potatoe | Trinidad & Tobago | Yes | 1994 |
| Frankie McIntosh | Producer of the Year | Producer | Plenty Wine | St. Vincent and the Grenadines | No | 1994 |
| Winston So So | Best New Male Artist | Artist | Plenty Wine | St Vincent | No | 1994 |
| Winston So So | Male Vocalist of the Year | Artist | Plenty Wine | St. Vincent and the Grenadines | No | 1994 |
| Frankie McIntosh | Arranger of the Year | Arranger | Plenty Wine | St. Vincent and the Grenadines | No | 1994 |
| Leston Paul | Producer of the Year | Producer | Paul | Trinidad & Tobago | No | 1994 |
| Leston Paul | Arranger of the Year | Arranger | Paul | Trinidad & Tobago | No | 1994 |
| Richie Francis | Best New Male Artist | Artist | Nobody Cares | Antigua | No | 1994 |
| Mackie Nelson | Producer of the Year | Producer | Mystery Band | Trinidad & Tobago | Yes | 1994 |
| Julian Williams | Producer of the Year | Producer | Mystery Band | Trinidad & Tobago | Yes | 1994 |
| Super Blue | Best Calypso of the Year | Artist | Flag Party | Trinidad & Tobago | No | 1995 |
| Eddie Grant & Super Blue | Producer of the Year | Producer | Flag Party | Barbados / Trinidad & Tobago | No | 1995 |
| Kenny J | Male Vocalist of the Year | Artist | D. Paint Brush | Trinidad & Tobago | No | 1995 |
| Flying Cloud | Best Party Calypso | Artist | Bacchanal | Grenada | No | 1995 |
| Sparrow | Male Vocalist of the Year | Artist | Age Is Just A Number | Trinidad & Tobago | No | 1995 |
| Sparrow | Best Social Commentary | Artist | Age Is Just A Number | Trinidad & Tobago | No | 1995 |
| Plenty Wine | Best Party Calypso | Artist | Winston So So | St. Vincent and the Grenadines | No | 1994 |
| United Sisters | Female Vocalist of the Year | Artist | Whoa Donkey | Trinidad & Tobago | No | 1994 |
| Doye Doye | Best Calypso of the Year | Artist | Wayne T & Silky Slim | Trinidad & Tobago | No | 1994 |
| Doye Doye | Best Party Calypso | Artist | Wayne T & Silky Slim | Trinidad & Tobago | No | 1994 |
| Designer | Male Vocalist of the Year | Artist | Up | Trinidad & Tobago | No | 1994 |
| Whoa Donkey | Best Calypso of the Year | Artist | United Sisters | Trinidad & Tobago | No | 1994 |
| Whoa Donkey | Best Party Calypso | Artist | United Sisters | Trinidad & Tobago | Yes | 1994 |
| Sparrow | Best Social Commentary | Artist | Try Again | Trinidad & Tobago | No | 1994 |
| Sparrow | Male Vocalist of the Year | Artist | Try Again | Trinidad & Tobago | Yes | 1994 |
| Mighty Spitfire (Calton Gumbs) / Mighty Unknown (Julian Pierre) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1994 |
| Calton Zigilee Constantine / George Yeates / Hugh Borde | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Steelband Music | | Trinidad & Tobago | Yes | 1994 |
| WITCO Desperadoes Steel Orchestra | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | 1994 Trinidad & Tobago Panorama Champions | | Trinidad & Tobago | Yes | 1994 |
| Geoffrey Holder | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Actor Painter Choreographer – Friend of the Art Award | | Trinidad & Tobago | Yes | 1994 |
| Singing Sonia | Female Vocalist of the Year | Artist | The Invasion | Trinidad & Tobago | No | 1994 |
| Julien Williams | Producer of the Year | Producer | Mother Earth Is Crying | Trinidad & Tobago | Yes | 1995 |
| Baron | Best Social Commentary | Artist | Mother Earth Is Crying | Trinidad & Tobago | No | 1995 |
| Baron | Male Vocalist of the Year | Artist | Mother Earth Is Crying | Trinidad & Tobago | Yes | 1995 |
| Leston Paul | Arranger of the Year | Arranger | Mother Earth Is Crying | Trinidad & Tobago | No | 1995 |
| Baron | Best Calypso of the Year | Artist | Mother Earth Is Crying | Trinidad & Tobago | Yes | 1995 |
| Kenny Phillips | Producer of the Year | Producer | Jump & Wave (Preacher) | Trinidad & Tobago | No | 1995 |
| Johnny King | Male Vocalist of the Year | Artist | Jump & Wave | Barbados | No | 1995 |
| Chris Allman & John King | Arranger of the Year | Arranger | Jump & Wave (John King) | Barbados | No | 1995 |
| Chris Allman & John King | Producer of the Year | Producer | Jump & Wave (John King) | Barbados / Barbados | No | 1995 |
| Kenny Phillips | Arranger of the Year | Arranger | Jump & Wave (Preacher) | Trinidad & Tobago | Yes | 1995 |
| Preacher | Best Party Calypso | Artist | Jump & Wave | Trinidad & Tobago | Yes | 1995 |
| Johnny King | Best Calypso of the Year | Artist | Jump & Wave | Barbados | No | 1995 |
| Preacher | Best Calypso of the Year | Artist | Jump & Wave | Trinidad & Tobago | No | 1995 |
| Johnny King | Best Party Calypso | Artist | Jump & Wave | Barbados | No | 1995 |
| Super Blue | Arranger of the Year | Arranger | Jab Malassie | Trinidad & Tobago | No | 1995 |
| Super Blue | Best Party Calypso | Artist | Jab Molassie | Trinidad & Tobago | No | 1995 |
| Randy Isaac | Best Social Commentary | Artist | Its A Paradise | Grenada | No | 1995 |
| Randy Isaac | Male Vocalist of the Year | Artist | Its A Paradise | Grenada | No | 1995 |
| Designer | Male Vocalist of the Year | Artist | Going De Distance | Trinidad & Tobago | No | 1995 |
| Peter Humphrey | Best Creative Humor | Artist | For Keith | St. Lucia | No | 1995 |
| Leroy Black Stalin Calliste | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | People’s Choice | | Trinidad & Tobago | Yes | 1995 |
| Samuel Brigo Abraham | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypsonian | | Trinidad & Tobago | Yes | 1995 |
| Kenny J. | Best Social Commentary | Artist | Tell Dem | Trinidad & Tobago | No | 1995 |
| Inspector | Best Calypso of the Year | Artist | Sweet Home | Grenada | No | 1995 |
| Inspector | Best Social Commentary | Artist | Sweet Home | Grenada | No | 1995 |
| Flying Cloud | Male Vocalist of the Year | Artist | Sweet Sweet Sweet | Grenada | No | 1995 |
| Winston Bailey | Producer of the Year | Producer | Poverty Is Hell | Trinidad & Tobago | No | 1995 |
| Shadow | Best Social Commentary | Artist | Poverty Is Hell | Trinidad & Tobago | Yes | 1995 |
| Shadow | Best Calypso of the Year | Artist | Poverty Is Hell | Trinidad & Tobago | No | 1995 |
| Leston Paul | Producer of the Year | Producer | Play Mr. Panist Play | Trinidad & Tobago | No | 1995 |
| DeFosto | Best Calypso of the Year | Artist | Play Mr. Panist Play | Trinidad & Tobago | No | 1995 |
| Poody | Best Creative Humor | Artist | Peeping Tom | Trinidad & Tobago | No | 1995 |
| Poody | Best Party Calypso | Artist | Peeping Tom | Trinidad & Tobago | No | 1995 |
| Prince Unique | Best Creative Humor | Artist | Ouch | Trinidad & Tobago | No | 1995 |
| David Rudder | Best Social Commentary | Artist | One Caribbean | Trinidad & Tobago | No | 1995 |
| Colin Lucas | Best Creative Humor | Artist | On She Cassette | Trinidad & Tobago | No | 1995 |
| Kitchener | Best Creative Humor | Artist | No Wuk For Carnival | Trinidad & Tobago | Yes | 1995 |
| Kitchener | Best Party Calypso | Artist | No Wuk For Carnival | Trinidad & Tobago | No | 1995 |
| Kitchener | Best Social Commentary | Artist | No Wuk For Carnival | Trinidad & Tobago | No | 1995 |
| Wizard | Best Calypso of the Year | Artist | New World Order | Grenada | No | 1995 |
| Tom Gonzales / Eddy Grant | Best Engineered Recording | Engineer | Dr. Cassandra | Barbados / Barbados | No | 1996 |
| Gabby | Male Vocalist of the Year | Artist | Dr. Cassandra | Barbados | Yes | 1996 |
| Anand Yankarran | Best Chutney-Soca Recording | Artist | Darling Ah Go Leave You | Trinidad & Tobago | No | 1996 |
| Chalkdust | Best Social Commentary | Artist | CNN Society | Trinidad & Tobago | No | 1996 |
| Heeralal Rampatar | Best Chutney-Soca Recording | Artist | Chutney Possey | Trinidad & Tobago | No | 1996 |
| Steve Sealy | Male Vocalist of the Year | Artist | Break Ah Way | Trinidad & Tobago | No | 1996 |
| Steve Sealy | Best Calypso of the Year | Artist | Break Ah Way | Trinidad & Tobago | No | 1996 |
| Sundar Popo | Best Chutney-Soca Recording | Artist | Bolo Gi | Trinidad & Tobago | No | 1996 |
| David Rudder | Producer of the Year | Producer | Another Day In Paradise | Trinidad & Tobago | No | 1996 |
| David Rudder | Arranger of the Year | Arranger | Another Day In Paradise | Trinidad & Tobago | No | 1996 |
| David Rudder | Best Calypso of the Year | Artist | Another Day In Paradise | Trinidad & Tobago | Yes | 1996 |
| David Rudder | Best Social Commentary | Artist | Another Day In Paradise | Trinidad & Tobago | Yes | 1996 |
| Calliston Pantor | Arranger of the Year | Arranger | Another Day In Paradise | Trinidad & Tobago | No | 1996 |
| Blacksand | Arranger of the Year | Arranger | Whistle | St. Vincent and the Grenadines | No | 1995 |
| Blacksand | Best Party Calypso | Artist | Whistle | St. Vincent and the Grenadines | No | 1995 |
| Emmanuel Cobo Jack Riley / Oscar Pile | The SUNSHINE Awards Hall of Fame(TM) | Inductees for Steelband Music | | Trinidad & Tobago | Yes | 1995 |
| Dictator (Kenneth St. Bernard) / Destroyer (Calton Glasgow) / Chalkdust (Dr. Hollis Liverpool) | The SUNSHINE Awards Hall of Fame(TM) | Inductees for Calypso Music | | Trinidad & Tobago | Yes | 1995 |
| Amoco Renegades | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Trinidad & Tobago Steelband Panorama Champions | | Trinidad & Tobago | Yes | 1995 |
| Sally Edwards | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Chutney-Soca | | Trinidad & Tobago | Yes | 1995 |
| Carl Jazzie Pantin | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Friend of the Art | | Trinidad & Tobago | Yes | 1995 |
| King Ajamu | Male Vocalist of the Year | Artist | On The Road Again | Grenada | No | 1996 |
| Nicholas Brancker | Arranger of the Year | Arranger | Obadele | Barbados | Yes | 1996 |
| Edwin Yearwood | Best Calypso of the Year | Artist | Obadele | Barbados | No | 1996 |
| Nicholas Brancker | Best Engineered Recording | Engineer | Obadele | Barbados | No | 1996 |
| Edwin Yearwood | Male Vocalist of the Year | Artist | Obadele | Barbados | No | 1996 |
| Nicholas Brancker | Producer of the Year | Producer | Obadele | Barbados | No | 1996 |
| Sally Edwards | Best Chutney-Soca Recording | Artist | Lotay Lah | Trinidad & Tobago | No | 1996 |
| Inspector | Best Calypso of the Year | Artist | Madness | Grenada | No | 1996 |
| Denise Belfon | Best Calypso of the Year | Artist | Kaka LeLe | Trinidad & Tobago | No | 1996 |
| John Affoon | Best Engineered Recording | Engineer | Kaka LeLe | Trinidad & Tobago | No | 1996 |
| Denise Belfon | Female Vocalist of the Year | Artist | Kaka LeLe | Trinidad & Tobago | No | 1996 |
| Leston Paul | Producer of the Year | Producer | Kaka LeLe | Trinidad & Tobago | No | 1996 |
| Rikki Jai | Best Chutney-Soca Recording | Artist | Koyal Bholeh Peecha Wadawa | Trinidad & Tobago | Yes | 1996 |
| David Rudder | Male Vocalist of the Year | Artist | Heaven | Trinidad & Tobago | No | 1996 |
| Crazy | Best Creative Humor | Artist | Finish It | Trinidad & Tobago | Yes | 1996 |
| Colin Lucas | Best Social Commentary | Artist | Don’t Hate | Trinidad & Tobago | No | 1996 |
| Singing Sonia | Female Vocalist of the Year | Artist | Don’t Hold | Trinidad & Tobago | No | 1996 |
| Eddy Grant | Arranger of the Year | Arranger | Dr. Cassandra | Barbados | No | 1996 |
| Gabby | Best Calypso of the Year | Artist | Dr. Cassandra | Barbados | No | 1996 |
| Charles dos Santos / David Ogrin | Best Engineered Recording | Engineer | Dr. Cassandra | Barbados / Barbados | No | 1996 |
| Red Plastic Bag | Best Social Commentary | Artist | Something In The Music | Barbados | No | 1996 |
| Stedson Plastic Bag Wiltshire | Producer of the Year | Producer | Something In The Music | Barbados | No | 1996 |
| Mac Fingal | Producer of the Year | Producer | Something In The Music | Barbados | No | 1996 |
| Red Plastic Bag | Best Calypso of the Year | Artist | Something In The Music | Barbados | No | 1996 |
| Nicholas Brancker | Arranger of the Year | Arranger | Something In The Music | Barbados | No | 1996 |
| Steadman Wiltshire | Arranger of the Year | Arranger | Something In The Music | Barbados | No | 1996 |
| Juiceman Roberts | Producer of the Year | Producer | Signal For Lara | Trinidad & Tobago | No | 1996 |
| Super Blue | Best Social Commentary | Artist | Signal For Lara | Trinidad & Tobago | No | 1996 |
| Juiceman Roberts | Arranger of the Year | Arranger | Signal for Lara | Trinidad & Tobago | No | 1996 |
| Super Blue | Best Calypso of the Year | Artist | Signal for Lara | Trinidad & Tobago | No | 1996 |
| Marcia Miranda | Female Vocalist of the Year | Artist | Raggamuffin Behavior | Trinidad & Tobago | Yes | 1996 |
| Designer | Male Vocalist of the Year | Artist | Pan In Manhattan | Trinidad & Tobago | Yes | 1996 |
| Colin Lucas | Best Creative Humor | Artist | One Foot Man | Trinidad & Tobago | No | 1996 |
| Emanuel Ector | Arranger of the Year | Arranger | On The Road | Trinidad & Tobago | No | 1996 |
| Ronnie McIntosh | Best Calypso of the Year | Artist | On The Road | Trinidad & Tobago | No | 1996 |
| Eric Michaud | Best Engineered Recording | Engineer | On The Road | Trinidad & Tobago | Yes | 1996 |
| King Ajamu | Best Social Commentary | Artist | On The Road | Grenada | No | 1996 |
| Emanuel Ector | Producer of the Year | Producer | On The Road | Trinidad & Tobago | No | 1996 |
| Austin Lyons | Producer of the Year | Producer | On The Road | Trinidad & Tobago | No | 1996 |
| Eric Michaud | Producer of the Year | Producer | On The Road | Trinidad & Tobago | No | 1996 |
| Swallow | Best Political Commentary | Artist | CDC | Antigua | Yes | 1997 |
| Shabaka | Best New Male Artist | Artist | Caribbean Voice | Trinidad & Tobago | No | 1997 |
| Canadian National Indian Orchestra | Best Chutney-Soca Recording | Artist | Bolo Ta Ra Ra | Canada | No | 1997 |
| Jaunty | Best Political Commentary | Artist | Bobolist | St. Lucia | No | 1997 |
| Jaunty | Best Creative Humor | Artist | Bobalist | St. Lucia | Yes | 1997 |
| Earl Brooks | Best Recording By A Pan Soloist | Pannist | Big Belly Man | Trinidad & Tobago | Yes | 1997 |
| David Rudder | Best Social Commentary | Artist | A Mad Man’s Rant | Trinidad & Tobago | No | 1997 |
| David Rudder | Best Calypso of the Year | Artist | A Mad Man’s Rant | Trinidad & Tobago | No | 1997 |
| Denyse Plummer | Female Vocalist of the Year | Artist | Your Woman | Trinidad & Tobago | No | 1996 |
| Singing Althea | Female Vocalist of the Year | Artist | Woman Plight | Antigua | No | 1996 |
| Richie Francis | Best Creative Humor | Artist | We Don’t Wave | Antigua | No | 1996 |
| Ossie Campbell / Sterling Betancourt | The SUNSHINE Awards Hall of Fame(TM) | Inductees for Steelband Music | | Trinidad & Tobago | Yes | 1996 |
| Viper (Roderick Lewis) / Lord Christo (Christopher Lidlow) / Viking (Victor Springer) | The SUNSHINE Awards Hall of Fame(TM) | Inductees for Calypso Music | | Trinidad & Tobago | Yes | 1996 |
| Kelvin Psycho Baptiste | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypsonian | | Trinidad & Tobago | Yes | 1996 |
| Emmanuel Young Killer Gilchrist | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypsonian | | Trinidad & Tobago | Yes | 1996 |
| Amoco Renegades | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | 1996 Trinidad & Tobago Panorama Champion | | Trinidad & Tobago | Yes | 1996 |
| Nickie Innis | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Friend of the Art Award | | Trinidad & Tobago | Yes | 1996 |
| David Rudder | Best Creative Humor | Artist | Trail of the Boomsie | Trinidad & Tobago | No | 1996 |
| Nicholas Brancker | Producer of the Year | Producer | Something In The Music | Barbados | No | 1996 |
| Nicholas Brancker | Best Engineered Recording | Engineer | Something In The Music | Barbados | No | 1996 |
| Ryan Romany | Producer of the Year | Producer | Chutney Bacchanal | Trinidad & Tobago | No | 1997 |
| Chris Garcia | Male Vocalist of the Year | Artist | Chutney Bacchanal | Trinidad & Tobago | No | 1997 |
| Chriss Garcia | Best Party Calypso | Artist | Chutney Bacchanal | Trinidad & Tobago | No | 1997 |
| Chris Garcia | Best New Male Artist | Artist | Chutney Bacchanal | Trinidad & Tobago | No | 1997 |
| Ryan Romany | Best Engineered Recording | Engineer | Chutney Bacchanal | Trinidad & Tobago | No | 1997 |
| Chris Garcia | Best Chutney-Soca Recording | Artist | Chutney Bacchanal | Trinidad & Tobago | Yes | 1997 |
| Ryan Romany | Arranger of the Year | Arranger | Chutney Bacchanal | Trinidad & Tobago | No | 1997 |
| Ajamu | Best Calypso of the Year | Artist | Christina | Grenada | No | 1997 |
| Ajamu | Male Vocalist of the Year | Artist | Christina | Grenada | Yes | 1997 |
| Kindred | Best Recording by a Group or Dance Band | Band | Celebration | Trinidad & Tobago | No | 1997 |
| Elsworth James | Best Calypso of the Year | Artist | Crabs In Ah Barrel | Canada | No | 1997 |
| Wendell Man Warren | Best Supporting Artists – Background Vocalists | Artist | Come Out of The Road Warrior | Trinidad & Tobago | No | 1997 |
| Stanton | Best Supporting Artists – Background Vocalists | Artist | Come Out of The Road Warrior | Trinidad & Tobago | No | 1997 |
| Roger Roberts | Best Supporting Artists – Background Vocalists | Artist | Come Out of The Road Warrior | Trinidad & Tobago | No | 1997 |
| John Issacs | Best Supporting Artists – Background Vocalists | Artist | Come Out of The Road Warrior | Trinidad & Tobago | No | 1997 |
| Chantwell | Best Rapso Recording | Artist | Clear De Way | Trinidad & Tobago | No | 1997 |
| Sharlene Boodram | Best Chutney-Soca Recording | Artist | Chutney Time | Trinidad & Tobago | No | 1997 |
| JMC Triveni | Best Recording by a Group or Dance Band | Band | Chutney Possey | Trinidad & Tobago | No | 1997 |
| Sandra Dopson | Best Supporting Artists – Background Vocalists | Artist | Chutney Bacchnal | | Yes | 1997 |
| Cheryl Seheult | Best Supporting Artists – Background Vocalists | Artist | Chutney Bacchnal | Trinidad & Tobago | Yes | 1997 |
| Ronnie McIntosh | Male Vocalist of the Year | Artist | Flying Time | Trinidad & Tobago | No | 1997 |
| Atlantik | Best Party Calypso | Artist | Follow Me | Trinidad & Tobago | No | 1997 |
| Atlantik | Best Recording by a Group or Dance Band | Band | Follow Me | Trinidad & Tobago | No | 1997 |
| Swallow | Best Calypso of the Year | Artist | Don’t Tease Me Tonight | Antigua | No | 1997 |
| Jason | Best Recording for Children | Artist | Dope Is Not The Answer | Canada | No | 1997 |
| Nicholas Brancker | Arranger of the Year | Arranger | Down De Road | Barbados | No | 1997 |
| Nicholas Brancker | Best Engineered Recording | Engineer | Down De Road | Barbados | No | 1997 |
| Edwin Yearwood | Best Party Calypso | Artist | Down De Road | Barbados | No | 1997 |
| Krosfyah | Best Recording by a Group or Dance Band | Band | Down De Road | Barbados | Yes | 1997 |
| Edwin Yearwood | Best Social Commentary | Artist | Down De Road | Barbados | No | 1997 |
| Nicholas Brancker | Producer of the Year | Producer | Down De Road | Barbados | No | 1997 |
| Lord Kitchener | Best Political Commentary | Artist | Election Day | Trinidad & Tobago | No | 1997 |
| Mac Fingal | Best Party Calypso | Artist | Ent Got Nothing | Barbados | No | 1997 |
| Marcia Miranda | Female Vocalist of the Year | Artist | Cyah Kill Kaiso | Trinidad & Tobago | Yes | 1997 |
| Marcia Miranda | Best Chutney-Soca Recording | Artist | Dance Doulahin Dance | Trinidad & Tobago | No | 1997 |
| Jason | Best Creative Humor | Artist | David’s Etiquette | Canada | No | 1997 |
| Marcia Miranda | Best Calypso of the Year | Artist | Dey Cyar Kill Kaiso | Trinidad & Tobago | No | 1997 |
| Kindred | Best Rapso Recording | Artist | Do You Like It | Trinidad & Tobago | No | 1997 |
| Joe Brown | Producer of the Year | Producer | Crabs In Ah Barrel | Trinidad & Tobago | No | 1997 |
| Elsworth James | Best Social Commentary | Artist | Crabs In Ah Barrel | Canada | No | 1997 |
| Denyse Plummer | Female Vocalist of the Year | Artist | Mind Yur Business | Trinidad & Tobago | No | 1997 |
| Ajamu | Best Recording for Children | Artist | Lets Get Serious | Grenada | No | 1997 |
| Carl Henderson | Arranger of the Year | Arranger | Jahaji Bhai | Trinidad & Tobago | Yes | 1997 |
| Carliste Roberts | Arranger of the Year | Arranger | Jahaji Bhai | Trinidad & Tobago | Yes | 1997 |
| Brother Marvin | Best Calypso of the Year | Artist | Jahaji Bhai | Trinidad & Tobago | Yes | 1997 |
| Brother Marvin | Best Chutney-Soca Recording | Artist | Jahaji Bhai | Trinidad & Tobago | No | 1997 |
| Carl Beaver Henderson | Best Engineered Recording | Engineer | Jahaji Bhai | Trinidad & Tobago | Yes | 1997 |
| Brother Marvin | Best Social Commentary | Artist | Jahaji Bhai | Trinidad & Tobago | Yes | 1997 |
| Carl Henderson | Producer of the Year | Producer | Jahaji Bhai | Trinidad & Tobago | Yes | 1997 |
| Taurus | Best New Male Artist | Artist | Jam of Class | Canada | No | 1997 |
| Gerald Charles | Best Recording By A Pan Soloist | Pannist | I Can See Clearly Now | Trinidad & Tobago | No | 1997 |
| Marilyn Joseph | Best New Female Vocalist | Artist | Identity Crisis | Trinidad & Tobago | Yes | 1997 |
| Andre Tanker | Producer of the Year | Producer | Here & Now | Trinidad & Tobago | No | 1997 |
| Andre Tanker | Male Vocalist of the Year | Artist | Here & Now | Trinidad & Tobago | No | 1997 |
| ZIN Band | The People’s Choice Award | Recipient | | Haiti | Yes | 1997 |
| Romena Ali | Best New Female Vocalist | Artist | Gup Chup Gup Chup | Canada | No | 1997 |
| Marie Brooks | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Dancer | | Guadeloupe | Yes | 1997 |
| Noel Richards | Best Gospelypso Recording by Duo or Group | Artist | Gospelypso | Trinidad & Tobago | No | 1997 |
| Small Island Pride (Theophilus Woods) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Grenada | Yes | 1997 |
| Ronnie McIntosh | Best Party Calypso | Artist | Flying Time | Trinidad & Tobago | No | 1997 |
| Genevieve Allard-Seals | Best Supporting Artists – Background Vocalists | Artist | Muevete | Trinidad & Tobago | No | 1997 |
| Monica Rogers | Best Supporting Artists – Background Vocalists | Artist | Muevete | Trinidad & Tobago | No | 1997 |
| Sabina Allard | Best Supporting Artists – Background Vocalists | Artist | Muevete | Trinidad & Tobago | No | 1997 |
| Sephernia Allard | Best Supporting Artists – Background Vocalists | Artist | Muevete | Trinidad & Tobago | No | 1997 |
| Nigel Lewis | Best Calypso of the Year | Artist | Moving | Trinidad & Tobago | No | 1997 |
| Nigel Lewis | Best New Male Artist | Artist | Moving | Trinidad & Tobago | Yes | 1997 |
| Nigel Lewis | Best Party Calypso | Artist | Moving | Trinidad & Tobago | Yes | 1997 |
| Nigel Lewis | Producer of the Year | Producer | Moving | Trinidad & Tobago | No | 1997 |
| Ossie Curly | Producer of the Year | Producer | Moving | Canada | No | 1997 |
| Nigel Lewis | Arranger of the Year | Arranger | Moving | Trinidad & Tobago | No | 1997 |
| Ossie Curly | Arranger of the Year | Arranger | Moving | Canada | No | 1997 |
| Sonny Mann | Best Chutney-Soca Recording | Artist | Lootala | Trinidad & Tobago | No | 1997 |
| Princess | Best New Female Vocalist | Artist | Love Me | Grenada | No | 1997 |
| Princess | Best Recording for Children | Artist | Love Me | Grenada | No | 1997 |
| Princess | Female Vocalist of the Year | Artist | Love Me | Grenada | No | 1997 |
| Ajamu | Best Social Commentary | Artist | Love Thy Neighbor | Grenada | No | 1997 |
| Sharlene Boodram | Best Soca-Parang Recording | Artist | Mamacita | Trinidad & Tobago | No | 1997 |
| Chalkdust | Best Political Commentary | Artist | Man In The Garden | Trinidad & Tobago | No | 1997 |
| Dread & The Baldhead | Best Creative Humor | Artist | Me D Ras | Antigua | No | 1997 |
| Denyse Plummer | Best Creative Humor | Artist | Mind Yur Business | Trinidad & Tobago | No | 1997 |
| Noel | Best Engineered Recording | Engineer | Soca Kingdom | USA | No | 1997 |
| Ajala | Male Vocalist of the Year | Artist | So Nanny So Nanny | Trinidad & Tobago | No | 1997 |
| Brian Morris | Best Engineered Recording | Engineer | So Nanny So Nanny | Trinidad & Tobago | No | 1997 |
| Panazz Players | Best Recording by Steelband Orchestra | Orchestra | Shadow of your Smile | Trinidad & Tobago | Yes | 1997 |
| Nigel Lewis | Best Recording for Children | Artist | Say A Prayer | Trinidad & Tobago | Yes | 1997 |
| Andre Tanker | Best Recording for Children | Artist | Sayamanda | Trinidad & Tobago | No | 1997 |
| Marcia Miranda | Best Social Commentary | Artist | Search For A Big Song | Trinidad & Tobago | No | 1997 |
| Quynton Gooding | Best New Male Artist | Artist | Remember When | Trinidad & Tobago | No | 1997 |
| Brother Resistance | Best Rapso Recording | Artist | Right Move | Trinidad & Tobago | Yes | 1997 |
| Nigel Ashby | Best New Male Artist | Artist | Remember When | Trinidad & Tobago | No | 1997 |
| Roots Steelband | Best Recording by Steelband Orchestra | Orchestra | Ready to go | Antigua | No | 1997 |
| Ajamu | Best Party Calypso | Artist | Push It Back | Grenada | No | 1997 |
| Crazy | Best Social Commentary | Artist | Put Your House In Order | Trinidad & Tobago | No | 1997 |
| Nigel Lewis | Best Rapso Recording | Artist | Puwah | Trinidad & Tobago | No | 1997 |
| Sharlene Boodram | Female Vocalist of the Year | Artist | Peace & Love | Trinidad & Tobago | No | 1997 |
| Barry Bartholomew | Arranger of the Year | Arranger | Panazz | Trinidad & Tobago | No | 1997 |
| Phase 11 Pan Grove | Best Recording by Steelband Orchestra | Orchestra | Pan Rising | Trinidad & Tobago | No | 1997 |
| Sammie C | Best Political Commentary | Artist | Nyaming We Money Free | Antigua | No | 1997 |
| Clive Bradley | Best Recording By A Pan Soloist | Pannist | My Cherie Amor | Trinidad & Tobago | No | 1997 |
| Brother Resistance | Best Political Commentary | Artist | Murderer | Trinidad & Tobago | No | 1997 |
| Sammie C | Best New Female Vocalist | Artist | Treat Me Nice | Antigua | No | 1997 |
| Swallow | Best Social Commentary | Artist | This Antigua | Antigua | No | 1997 |
| Crazy | Best Party Calypso | Artist | This Is Madness | Trinidad & Tobago | No | 1997 |
| Mighty Terror (Fitzgerald Henry) / Lord Burgis (Irving Burgie) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Tinidad & Tobago / USA | Yes | 1997 |
| Ajamu | Best Soca-Parang Recording | Artist | The Parang Band | Grenada | No | 1997 |
| David Rudder | Best Political Commentary | Artist | The Strange Tale of Madame Occhahontas | Trinidad & Tobago | No | 1997 |
| Andy Narell | Best Engineered Recording | Engineer | Thanks To D Music | USA | No | 1997 |
| Frank Agarrat | Best Engineered Recording | Engineer | Thanks To D Music | Trinidad & Tobago | No | 1997 |
| Zahir Khan | Best Engineered Recording | Engineer | Thanks To D Music | Trinidad & Tobago | No | 1997 |
| D Rebels Band | Best Recording by a Group or Dance Band | Band | The Car Key | St. Vincent and the Grenadines | No | 1997 |
| Sammie C | Female Vocalist of the Year | Artist | Terror and The Madness | Antigua | No | 1997 |
| Xtatik | Best Party Calypso | Artist | Take Ah Borrow | Trinidad & Tobago | No | 1997 |
| Xtatik | Best Recording by a Group or Dance Band | Band | Take Ah Borrow | Trinidad & Tobago | No | 1997 |
| Edwin Yearwood | Male Vocalist of the Year | Artist | Something Greater | Barbados | No | 1997 |
| Edwin Yearwood | Best Recording for Children | Artist | Something Greater | Barbados | No | 1997 |
| Edwin Yearwood | Best Calypso of the Year | Artist | Something Greater | Barbados | No | 1997 |
| Swallow | Male Vocalist of the Year | Artist | Soca Kingdom | Antigua | No | 1997 |
| Rolling Tones | Best Party Calypso | Artist | Soca Man | St Maarten | No | 1997 |
| Rolling Tones | Best Recording by a Group or Dance Band | Band | Soca Man | St. Maarten | No | 1997 |
| David English | Best Engineered Recording | Engineer | Soca Kingdom | USA | No | 1997 |
| Xtatik | Best Recording by a Group or Dance Band | Band | Big Truck | Trinidad & Tobago | Yes | 1998 |
| JMC Triveni | Best Chutney-Soca Recording | Artisit | Basmatie | Trinidad & Tobago | Yes | 1998 |
| Asophonics | Best Recording by Steelband Orchestra | Orchestra | Be Still My Soul | Trinidad & Tobago | No | 1998 |
| Atlantik | Best Recording by a Group or Dance Band | Band | All Aboard | Trinidad & Tobago | No | 1998 |
| Atlantik | Best Party Calypso | Artisit | All Aboard | Trinidad & Tobago | No | 1998 |
| Nicholas Brancker | Arranger of the Year | Arranger | All Aboard | Barbados | No | 1998 |
| Atlantik | Best Calypso of the Year | Artisit | All Aboard | Trinidad & Tobago | No | 1998 |
| Kenny J | Best Soca-Parang Recording | Artisit | Alexander | Trinidad & Tobago | Yes | 1998 |
| Kenny J | Best Creative Humor | Artisit | Alexander | Trinidad & Tobago | No | 1998 |
| Marilyn Joseph | Best Gospelypso Recording by Duo or Group | Artist | Woman of Integrity | Trinidad & Tobago | No | 1997 |
| Ken Philmore | Best Recording By A Pan Soloist | Pannist | What’s Going On | Trinidad & Tobago | No | 1997 |
| J. Errol Lewis | Best Gospelypso Recording by Duo or Group | Artist | When We All Get To Heaven | Trinidad & Tobago | Yes | 1997 |
| Resistance | Best Gospelypso Recording by Duo or Group | Artist | When We All Get To Heaven | Trinidad & Tobago | Yes | 1997 |
| Los Dinamicos | Best Soca-Parang Recording | Artist | We Parang Now | Trinidad & Tobago | Yes | 1997 |
| Leston Paul | Arranger of the Year | Arranger | Weakness for Sweetness | Trinidad & Tobago | No | 1997 |
| Black James (Norman James) / Fisheye (Rudolph Olivierre) | The SUNSHINE Awards Hall of Fame(TM) | Inductees for Steelband Music | | Trinidad & Tobago | Yes | 1997 |
| Ed Watson | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Musician Songwriter Arranger & Producer | | Trinidad & Tobago | Yes | 1997 |
| Amoco Renegades | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Trinidad & Tobago Steelband Panorama Champion | | Trinidad & Tobago | Yes | 1997 |
| Black Stalin | The People’s Choice Award | Calypsonian | | Trinidad & Tobago | Yes | 1997 |
| Robert Greenidge | Best Recording By A Pan Soloist | Pannist | Trini Style | Trinidad & Tobago | No | 1997 |
| Joe Brown | Producer of the Year | Producer | Ent?? | Trinidad & Tobago | Yes | 1998 |
| Connector | Best New Male Artist | Artisit | Dance | Canada | No | 1998 |
| Victorio | Best Creative Humor | Artisit | Doctor | Canada | No | 1998 |
| Onyan | Producer of the Year | Producer | Crazyman | Antigua | No | 1998 |
| Onyan | Male Vocalist of the Year | Artisit | Congo Line | Antigua | No | 1998 |
| Sundar Popo | Best Chutney-Soca Recording | Artisit | Chalbo Kihahi | Trinidad & Tobago | No | 1998 |
| Annan Yankaran | Best Chutney-Soca Recording | Artisit | Caura River | Trinidad & Tobago | No | 1998 |
| Chalkdust | Best Political Commentary | Artisit | Caribbean Leaders | Trinidad & Tobago | No | 1998 |
| Clifton Bomber Ryan | The SUNSHINE Awards Hall of Fame(TM) | Recipient | Calypso | | Yes | 1998 |
| Carlton Lord Blakie Joseph | The SUNSHINE Awards Hall of Fame(TM) | Recipient | Calypso | | Yes | 1998 |
| Skiffle Bunch | Best Recording by Steelband Orchestra | Orchestra | Call to the Ancestors | Trinidad & Tobago | Yes | 1998 |
| 3 Canal | Best Recording by a Group or Dance Band | Band | Blue | Trinidad & Tobago | No | 1998 |
| 3 Canal | Best New Male Artist | Artisit | Blue | Trinidad & Tobago | No | 1998 |
| 3 Canal | Best Rapso Recording | Artisit | Blue | Trinidad & Tobago | Yes | 1998 |
| Sheldon Benjamin & Machel Montano | Arranger of the Year | Arranger | Big Truck | Trinidad & Tobago | No | 1998 |
| Frankie McIntosh | Arranger of the Year | Arranger | Big Fly | St. Vincent and the Grenadines | Yes | 1998 |
| Beckett | Best Party Calypso | Artisit | Big Fly | St. Vincent and the Grenadines | No | 1998 |
| Becket | Male Vocalist of the Year | Artisit | Big Fly | St. Vincent and the Grenadines | No | 1998 |
| Frankie McIntosh | Producer of the Year | Producer | Big Fly | St. Vincent and the Grenadines | No | 1998 |
| Machel Montano | Best Party Calypso | Artisit | Big Truck | Trinidad & Tobago | Yes | 1998 |
| Kitchener | Best Political Commentary | Artisit | No Wuk Band | Trinidad & Tobago | No | 1998 |
| Carl Beaver Henderson | Producer of the Year | Music Producer | Nah Leaving | Trinidad & Tobago | Yes | 1998 |
| Melanie Hudson | Female Vocalist of the Year | Artisit | My Calypso | Trinidad & Tobago | No | 1998 |
| Chantwell | Best Rapso Recording | Artisit | Morning Ground | Trinidad & Tobago | No | 1998 |
| Denyse Plummer | Female Vocalist of the Year | Artisit | Misbehave | Trinidad & Tobago | Yes | 1998 |
| Gypsy | Best Recording for Children | Artisit | Little Black Boys | Trinidad & Tobago | Yes | 1998 |
| Gypsy | Best Social Commentary | Artisit | Little Black Boys | Trinidad & Tobago | No | 1998 |
| Roots Steelband | Best Recording by Steelband Orchestra | Orchestra | Jenny | Antigua | No | 1998 |
| Carlene Davis | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Contribution to Caribbean Music | | Jamaica | Yes | 1998 |
| Rita Marley | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Contribution to Caribbean Music | | Jamaica | Yes | 1998 |
| Swallow | Best Political Commentary | Artisit | Its About Time | Antigua | No | 1998 |
| Dread & The Baldhead | Best Creative Humor | Artisit | Hard Wurk | Antigua | No | 1998 |
| The Phantoms | The People’s Choice Award | Band | | Haiti | Yes | 1998 |
| Dennis DeSouza | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Contribution to Caribbean Music | | Guyana | Yes | 1998 |
| Dread & The Baldhead | Best Recording for Children | Artisit | God Is Love | Antigua | No | 1998 |
| Nigel Lewis | Best Party Calypso | Artisit | Follow The Leader | Trinidad & Tobago | No | 1998 |
| Traffik | Best Recording by a Group or Dance Band | Band | Down Sando | Trinidad & Tobago | No | 1998 |
| Ronnie McIntosh | Male Vocalist of the Year | Artisit | Ent | Trinidad & Tobago | Yes | 1998 |
| Ronnie McIntosh | Best Party Calypso | Artisit | Ent?? | Trinidad & Tobago | No | 1998 |
| Ronnie McIntosh | Best Rapso Recording | Artisit | Ent?? | Trinidad & Tobago | No | 1998 |
| Figgy | Best New Male Artist | Artisit | Soca Pilgrimage | St. Thomas USVI | No | 1998 |
| General Grant | Best Rapso Recording | Artisit | Soca Billboard | Trinidad & Tobago | No | 1998 |
| Krosfyah | Best Party Calypso | Artisit | Road Block | Barbados | No | 1998 |
| Krosfyah | Best Recording by a Group or Dance Band | Band | Road Block | Barbados | No | 1998 |
| Krosfyah | Best Recording for Children | Artisit | Redemption | Barbados | No | 1998 |
| Krosfyah | Best Social Commentary | Artisit | Redemption | Barbados | No | 1998 |
| Nicholas Brancker | Producer of the Year | Producer | Redemption | Barbados | No | 1998 |
| Victorio | Best New Male Artist | Artisit | Rainbow | Canada | Yes | 1998 |
| Victorio | Best Social Commentary | Artisit | Rainbow People | Canada | No | 1998 |
| Carlysle Roberts | Producer of the Year | Producer | People of the Earth | Trinidad & Tobago | No | 1998 |
| Black Stalin | Best Social Commentary | Artisit | People of the Earth | Trinidad & Tobago | Yes | 1998 |
| Carlysle Roberts | Arranger of the Year | Arranger | People of the Earth | Trinidad & Tobago | No | 1998 |
| Black Stalin | Best Calypso of the Year | Artisit | People of the Earth | Trinidad & Tobago | Yes | 1998 |
| Black Stalin | Best Recording for Children | Artisit | People of the Earth | Trinidad & Tobago | No | 1998 |
| Designer | Male Vocalist of the Year | Artisit | Pan Is Money | Trinidad & Tobago | No | 1998 |
| Leston Paul | Arranger of the Year | Arranger | Pan In Town | Trinidad & Tobago | No | 1998 |
| DeFosto | Best Calypso of the Year | Artisit | Pan In Town | Trinidad & Tobago | No | 1998 |
| Singing Sandra | Female Vocalist of the Year | Artisit | One Destiny | Trinidad & Tobago | No | 1998 |
| Sugar Aloes | Best Political Commentary | Artisit | One Caribbean | Trinidad & Tobago | Yes | 1998 |
| Singing Sandra | Best Social Commentary | Artisit | One Destiny | Trinidad & Tobago | No | 1998 |
| Krosfyah | Best Party Calypso | Artist | Appetite | Barbados | No | 1999 |
| Krosfyah | Best Recording by a Group or Dance Band | Band | Appetite | Barbados | No | 1999 |
| Errol Fabien | Best New Male Artist | Artist | Ato Tea Party | Trinidad & Tobago | Yes | 1999 |
| Zin | Best Caribbean / French-Creole Pop-Ballad Recording | Artist | All I Want | Haiti | Yes | 1999 |
| Sammie C | Best Political Commentary | Artisit | We Great Too-VC | Antigua | No | 1998 |
| Bally | Best Calypso of the Year | Artisit | We Coming Back | Trinidad & Tobago | No | 1998 |
| Ajamu | Male Vocalist of the Year | Artisit | Wadada | Grenada | No | 1998 |
| Twiggy | Female Vocalist of the Year | Artisit | Up Under Me | Trinidad & Tobago | No | 1998 |
| The United Nations Singers | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Special Recognition for Contribution to World Music | | USA | Yes | 1998 |
| Sprangalang | Best Creative Humor | Artisit | Two Cords | Trinidad & Tobago | Yes | 1998 |
| Kim Johnson | The SUNSHINE Award for Journalism | Trinidad & Tobago Express Newspaper Journalist | | Trinidad & Tobago | Yes | 1998 |
| David Rudder | The People’s Choice Award | Artist | | Trinidad & Tobago | Yes | 1998 |
| The Mighty Sparrow | Lifetime Achievement Award | Calypsonian | | Trinidad & Tobago | Yes | 1998 |
| Peter Minshall | Friend of the Arts SUNSHINE Award | Contribution to Caribbean Art & Dance | | Trinidad & Tobago | Yes | 1998 |
| Chalkdust | Best Social Commentary | Artisit | The New Menu | Trinidad & Tobago | No | 1998 |
| Los Amigos De Jesus | Best Soca-Parang Recording | Artisit | The Meaning of Christmas | Trinidad & Tobago | No | 1998 |
| Kitchener | Best Calypso of the Year | Artisit | The Guitar Pan | Trinidad & Tobago | No | 1998 |
| Cecil Catarrh Nose Augustine | The SUNSHINE Awards Hall of Fame(TM) | Recipient | Steelband | | Yes | 1998 |
| Bertie Marshall | The SUNSHINE Awards Hall of Fame(TM) | Recipient | Steelband | | Yes | 1998 |
| Leon Coldero | Best Chutney-Soca Recording | Artisit | Spicy & Peppery | Trinidad & Tobago | No | 1998 |
| Rikki Jai | Best Chutney-Soca Recording | Artist | Dulahin | Trinidad & Tobago | No | 1999 |
| Singing Sandra | Best Creative Humor | Artist | Equalizer | Trinidad & Tobago | No | 1999 |
| Lady Spencer | Best Rapso Recording | Artist | D Ring Bi Ding Song | Trinidad & Tobago | No | 1999 |
| Square One | Best Party Calypso | Artist | DJ Ride | Barbados | No | 1999 |
| Allison Hinds | Female Vocalist of the Year | Artist | DJ Ride | Barbados | No | 1999 |
| Ozzie Gurley | Arranger of the Year | Arranger | Doh Promise | Canada | No | 1999 |
| Singing Althea | Best Political Commentary | Artist | Choices | Antigua | No | 1999 |
| Gypsy | Best Recording for Children | Artist | Children of the Revolution | Trinidad & Tobago | Yes | 1999 |
| Denyse Plummer | Female Vocalist of the Year | Artist | Carnival Queen | Trinidad & Tobago | No | 1999 |
| King Zacari | Best Political Commentary | Artist | Cari Com | Antigua | No | 1999 |
| General Val | Best New Male Artist | Artist | Caribbean Woman | St. Thomas | No | 1999 |
| General Val | Male Vocalist of the Year | Artist | Caribbean Woman | St. Thomas | No | 1999 |
| Singing Francine | Female Vocalist of the Year | Artist | Carnival In My Land | Barbados | No | 1999 |
| Kenneth Seepersad | Best Chutney-Soca Recording | Artist | Bonjay | Trinidad & Tobago | No | 1999 |
| T-Vice | Best Caribbean / French-Creole Pop-Ballad Recording | Artist | Bidi Bidi Bam Bam | France | No | 1999 |
| Mystic Prowler | Best Calypso of the Year | Artist | Below The Surface | Trinidad & Tobago | No | 1999 |
| Mystic Prowler | Best Recording for Children | Artist | Below The Surface | Trinidad & Tobago | No | 1999 |
| Mystic Prowler | Best Social Commentary | Artist | Below The Surface | Trinidad & Tobago | No | 1999 |
| Mystic Prowler | Male Vocalist of the Year | Artist | Below The Surface | Trinidad & Tobago | No | 1999 |
| Singing Francine | Best Creative Humor | Artist | Bajan Talk | Barbados | No | 1999 |
| King Cosmos | Best New Male Artist | Artist | Jammin-Dis One Hot | Canada | No | 1999 |
| David Rudder | Producer of the Year | Producer | High Mas | Trinidad & Tobago | Yes | 1999 |
| Leston Paul | Arranger of the Year | Arranger | How It Go Look | Trinidad & Tobago | No | 1999 |
| Joe Brown | Producer of the Year | Producer | How It Go Look | Trinidad & Tobago | No | 1999 |
| Leston Paul | Producer of the Year | Producer | How It Go Look | Trinidad & Tobago | No | 1999 |
| Kindred | Best Rapso Recording | Artist | I Believe | Trinidad & Tobago | No | 1999 |
| David Rudder | Male Vocalist of the Year | Artist | High Mas | Trinidad & Tobago | Yes | 1999 |
| David Rudder | Best Social Commentary | Artist | High Mas | Trinidad & Tobago | Yes | 1999 |
| Exodust | Best Recording by Steelband Orchestra | Orchestra | High Mas | Trinidad & Tobago | No | 1999 |
| Wayne Bruno | Arranger of the Year | Arranger | High Mas | Trinidad & Tobago | Yes | 1999 |
| David Rudder | Best Calypso of the Year | Artist | High Mas | Trinidad & Tobago | Yes | 1999 |
| David Rudder | Best Party Calypso | Artist | High Mas | Trinidad & Tobago | No | 1999 |
| Celia Samaroo | Best Chutney-Soca Recording | Artist | Gimme Chutney | Guyana | No | 1999 |
| Rolling Tones | Best Party Calypso | Artist | Flag Zone | St. Maarten | No | 1999 |
| Wayne Rodriguez | Best Party Calypso | Artist | Foorsteps | Trinidad & Tobago | Yes | 1999 |
| Wayne Rodriguez | Best Calypso of the Year | Artist | Footsteps | Trinidad & Tobago | No | 1999 |
| Black Lyrics | Best Rapso Recording | Artist | Feeling Woi Woi | Trinidad & Tobago | No | 1999 |
| Sheldon Webster | Producer of the Year | Producer | Feelin Good | Trinidad & Tobago | No | 1999 |
| Barry Bartholomew | Producer of the Year | Producer | Feelin Good | Trinidad & Tobago | No | 1999 |
| Singing Sandra | Female Vocalist of the Year | Artist | Equalizer | Trinidad & Tobago | No | 1999 |
| Nicholas Brancker | Arranger of the Year | Arranger | Kitty Cat | Barbados | No | 1999 |
| Square One | Best Calypso of the Year | Artist | Kitty Cat | Barbados | No | 1999 |
| Square One | Best Recording by a Group or Dance Band | Band | Kitty Cat | Barbados | Yes | 1999 |
| Nicholas Brancker | Producer of the Year | Producer | Kitty Cat | Barbados | No | 1999 |
| Jaunty | Best Caribbean / French-Creole Pop-Ballad Recording | Artist | Ladje Mwem | St. Lucia | No | 1999 |
| Denyse Plummer | Best Recording for Children | Artist | Legend Lord Kitchener | Trinidad & Tobago | No | 1999 |
| Sharlene Boodram | Best Caribbean / French-Creole Pop-Ballad Recording | Artist | Pour Un Ami | Trinidad & Tobago | No | 1999 |
| Gypsy | Best Social Commentary | Artist | Pick Yourself Up | Trinidad & Tobago | No | 1999 |
| Mystic Prowler | Best Creative Humor | Artist | PC Man | Trinidad & Tobago | No | 1999 |
| Amoco Renegades | Best Recording by Steelband Orchestra | Orchestra | Pan For Carnival | Trinidad & Tobago | No | 1999 |
| Panazz | Best Recording by Steelband Orchestra | Orchestra | Old Lady Walk A Mile | Trinidad & Tobago | No | 1999 |
| Starliff | Best Recording by Steelband Orchestra | Orchestra | O’Trinidad | Trinidad & Tobago | No | 1999 |
| Roots Steelband | Best Recording by Steelband Orchestra | Orchestra | Oh When the Saints | Antigua | No | 1999 |
| Osha | Best Recording for Children | Artist | Number One | USVI | No | 1999 |
| 3-Canal | Best Rapso Recording | Artist | Mud Maddness | Trinidad & Tobago | Yes | 1999 |
| Jaunty | Best Social Commentary | Artist | Mothers Feel The Pain | St. Lucia | No | 1999 |
| Jaunty | Best Recording for Children | Artist | Mothers Feel The Pain | St. Lucia | No | 1999 |
| Frankie McIntosh | Arranger of the Year | Arranger | Maria | St. Vincent and the Grenadines | No | 1999 |
| Trinidad All Stars | Best Recording by Steelband Orchestra | Orchestra | Me and Mih Lady | Trinidad & Tobago | Yes | 1999 |
| Onyan | Male Vocalist of the Year | Artist | Life In The Ghetto | Antigua | No | 1999 |
| Red Plastic Bag | Best Calypso of the Year | Artist | What Kind of World | Barbados | No | 1999 |
| Plastic Bag | Best Social Commentary | Artist | What Kind of World | Barbados | Yes | 1999 |
| Plastic Bag | Male Vocalist of the Year | Artist | What Kind of World | Barbados | No | 1999 |
| Sydney Gollop / Hazel Henley | The SUNSHINE Awards Hall of Fame(TM) | Inductees for Steelband Music | | Trinidad & Tobago | Yes | 1999 |
| David Rudder | The People’s Choice Award | Calypsonian | | Trinidad & Tobago | Yes | 1999 |
| Desperadoes Steel orchestra | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | 1999 Trinidad & Tobago Panorama Champions | | Trinidad & Tobago | Yes | 1999 |
| Grace Blake | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Contribution to the Arts | | Trinidad & Tobago | Yes | 1999 |
| Lord Brynner (Kade Simon) | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1999 |
| Nap Hepburn and the March of Dimes | The SUNSHINE Awards Hall of Fame(TM) | Inductee for Calypso Music | | Trinidad & Tobago | Yes | 1999 |
| Young Killer (Emmanuel Daniel Jardine Gilchrist) | The SUNSHINE Awards Hall of Fame(TM) | Inductees for Calypso Music | | Trinidad & Tobago | Yes | 1999 |
| Xtatik | Best Recording by a Group or Dance Band | Band | Toro Toro | Trinidad & Tobago | No | 1999 |
| Zin | Best Recording by a Group or Dance Band | Band | Ti Randevou | Haiti | No | 1999 |
| Chalkdust | Best Political Commentary | Artist | The New Menu | Trinidad & Tobago | No | 1999 |
| Kitchener | Best Calypso of the Year | Artist | Symphony On The Street | Trinidad & Tobago | No | 1999 |
| Atlantik | Best Recording by a Group or Dance Band | Band | Suzanna | Trinidad & Tobago | No | 1999 |
| Dr. Hans Geiser | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Friend of the Art | | Switzerland | Yes | 1999 |
| Phantoms | Best Caribbean / French-Creole Pop-Ballad Recording | Artist | Sonje | Haiti | No | 1999 |
| Triveni | Best Chutney-Soca Recording | Artist | Rool It Batie | Trinidad & Tobago | Yes | 1999 |
| Nydia Caro | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Contribution to Caribbean Latin Music | | Puerto Rico | Yes | 1999 |
| Kanchan | Best Chutney-Soca Recording | Artist | Radha Kaniya | India | No | 1999 |
| George Lamaond | Best Caribbean / Latin Tropical Album | Artist | Emtrega | Puerto Rico | No | 2000 |
| Joel Connector Davis | Best Gospelypso Recording by Duo or Group | Artist | De Nation Cries | Canada | No | 2000 |
| Connector | Best Social Commentary | Artist | De Nations Cries | Canada | No | 2000 |
| Sanell Dempster | Female Vocalist of the Year | Artist | De River | Trinidad & Tobago | Yes | 2000 |
| Terrance James | Arranger of the Year | Arranger | De River | Trinidad & Tobago | No | 2000 |
| Terrance James | Producer of the Year | Producer | De River | Trinidad & Tobago | No | 2000 |
| Sanell Dempster | Calypso of the Year | Artist | De River | Trinidad & Tobago | No | 2000 |
| Sanell Dempster | Best Party Calypso | Artist | De River | Trinidad & Tobago | No | 2000 |
| Strings | Best Recording by a Group or Dance Band | Band | Carnival Tropical | Haiti | No | 2000 |
| Karega Mandella | Best Rapso Recording | Artist | Carnival Is | Trinidad & Tobago | No | 2000 |
| Marcia Miranda | Best Soca-Parang Recording | Artist | Bring Out De Ham | Trinidad & Tobago | No | 2000 |
| Red Plastic Bag | The People’s Choice Award | Artist | | Barbados | No | 2000 |
| Los Dinamicos | Best Soca-Parang Recording | Group | Back A Yard | Trinidad & Tobago | No | 2000 |
| Krosfyah | Best Recording by a Group or Dance Band | Band | Appetite | Barbados | No | 2000 |
| Singing Althea | Best Social Commentary | Artist | Violence | Antigua | No | 1999 |
| Singing Althea | Female Vocalist of the Year | Artist | Violence | Antigua | Yes | 1999 |
| Mystic Prowler | Best Political Commentary | Artist | Year 2010 / Version of TnT | Trinidad & Tobago | Yes | 1999 |
| 3rd Bass | Best Rapso Recording | Artist | Woman | Trinidad & Tobago | No | 1999 |
| Errol Ince | Arranger of the Year | Arranger | Willie Dead | Trinidad & Tobago | No | 1999 |
| Sparrow | Best Creative Humor | Artist | Willie Dead | Trinidad & Tobago | Yes | 1999 |
| Los Dinamicos | Best Caribbean / Latin Tropical Album | Group | Latino Soca Parranda | Trinidad & Tobago | No | 2000 |
| Crazy | Best Political Commentary | Artist | Leaders | Trinidad & Tobago | No | 2000 |
| Sam | Best New Male Artist | Artist | Jazz Up the Soca | USA | No | 2000 |
| Panazz Steel Orchestra | Best Recording by Steelband Orchestra | Orchestra | House t House Medley | Trinidad & Tobago | Yes | 2000 |
| Babla & Kanchan | Best Chutney-Soca Recording | Artist | Hum Na Jaibe | India | No | 2000 |
| Kenny J | Best Soca-Parang Recording | Artist | Hush Yur Mouth | Trinidad & Tobago | No | 2000 |
| Nikki Crosby | Best Creative Humor | Artist | I Learn To Wine | Trinidad & Tobago | No | 2000 |
| Mystic Prowler | Calypso of the Year | Artist | Healing of A Nation | Trinidad & Tobago | No | 2000 |
| Mystic Prowler | Male Vocalist of the Year | Artist | Healing of a Nation | Trinidad & Tobago | No | 2000 |
| Brother Resistance | Best Rapso Recording | Artist | Handclapping Song | Trinidad & Tobago | No | 2000 |
| Anand Yankaran | Best Chutney-Soca Recording | Artist | Habada Lakay Anah | Trinidad & Tobago | No | 2000 |
| Sybil Chester | Friend of the Arts SUNSHINE Award | Friend of the Art | | Guyana | Yes | 2000 |
| Noel Professor Richards | Best Rapso Recording | Artist | God Is Good | Trinidad & Tobago | No | 2000 |
| Tallpree | The People’s Choice Award | Artist | | Grenada | Yes | 2000 |
| Shurwayne Winchester | Best New Male Artist | Artist | Get Out of My Dreams | Trinidad & Tobago | Yes | 2000 |
| Shurwayne Winchester | Male Vocalist of the Year | Artist | Get Out Of My Dreams | Trinidad & Tobago | Yes | 2000 |
| Strings | Best Caribbean / French-Creole Tropical Album | Band | Flamenco Tropical | Haiti | Yes | 2000 |
| Scrunter | Best Soca-Parang Recording | Artist | Drinking Anything | Trinidad & Tobago | Yes | 2000 |
| Drupatee | Female Vocalist of the Year | Artist | Drupatee Style | Trinidad & Tobago | No | 2000 |
| Drupatee | Best Chutney-Soca Recording | Artist | Drupatee Style | Trinidad & Tobago | Yes | 2000 |
| Noel Professor Richards | Best Gospelypso Recording by Duo or Group | Artist | Savavvah | Trinidad & Tobago | No | 2000 |
| Wilkins Velez | Best Caribbean / Latin Tropical Album | Artist | Saque Bombom | Puerto Rico | No | 2000 |
| K Dans | Best Caribbean / French-Creole Tropical Album | Artist | S. O. S. | France | No | 2000 |
| Marilyn Destiny Joseph | Best Gospelypso Recording by Duo or Group | Artist | Rejoice | Trinidad & Tobago | Yes | 2000 |
| Funny | Calypso of the Year | Artist | Read Something | Trinidad & Tobago | No | 2000 |
| Funny | Best Recording for Children | Artist | Read Something | Trinidad & Tobago | Yes | 2000 |
| George Lamond | Best New Male Artist | Artist | Que Te Vas | Puerto Rico | No | 2000 |
| Nodley Frederick | Best Engineered Recording | Engineer | Old Woman Alone | Grenada | No | 2000 |
| Nodley Frederick | Arranger of the Year | Arranger | Old Woman Alone | Grenada | No | 2000 |
| Nodley Frederick | Producer of the Year | Producer | Old Woman Alone | Grenada | No | 2000 |
| Tallpree | Best Party Calypso | Artist | Old Woman Alone | Grenada | Yes | 2000 |
| Singing Althea | Female Vocalist of the Year | Artist | Nice Time | Antigua | No | 2000 |
| Triveni | Best Chutney-Soca Recording | Band | Morbalam | Trinidad & Tobago | No | 2000 |
| Pamberi Steel Orchestra | Best Recording by Steelband Orchestra | Orchestra | Mission Impossible | Trinidad & Tobago | No | 2000 |
| Viento De Agua | Best Caribbean / Latin Tropical Album | Band | Lo Que Le Gosta A La Gente | Puerto Rico | Yes | 2000 |
| Singing Francine | Best Social Commentary | Artist | Love Your Mother | Barbados | No | 2000 |
| Marilyn Joseph | Best Recording for Children | Artist | Let Me Be Your Friend | Trinidad & Tobago | No | 2000 |
| Zin | Best Caribbean / French-Creole Tropical Album | Band | Kanpe Sou Yon Bit | Haiti | No | 2000 |
| Nigel & Marvin Lewis | Best Recording for Children | Artist | Keep The Faith | Trinidad & Tobago | No | 2000 |
| Skandal | Best Caribbean / French-Creole Tropical Album | Artist | Lakou Lakay | Haiti | No | 2000 |
| Square One | Best Recording by a Group or Dance Band | Band | Togetherness | Barbados | No | 2000 |
| Lord Kitchener | Best Social Commentary | Artist | Toco Band | Trinidad & Tobago | No | 2000 |
| Funny | Best Creative Humor | Artist | Time Really Flies | Trinidad & Tobago | Yes | 2000 |
| Bill Newman | Best New Male Artist | Artist | Talk Shows | Canada | No | 2000 |
| Bill Newman | Best Creative Humor | Artist | Talk Shows | Canada | No | 2000 |
| 3 Canal | Best Political Commentary | Artist | Talk Yur Talk | Trinidad & Tobago | Yes | 2000 |
| 3 Canal | Best Engineered Recording | Group | Talk Yur Talk | Trinidad & Tobago | No | 2000 |
| Sheldon Benjamine | Arranger of the Year | Arranger | Talk Yur Talk | Trinidad & Tobago | No | 2000 |
| 3 Canal | Producer of the Year | Producers | Talk Yur Talk | Trinidad & Tobago | No | 2000 |
| 3 Canal | Best Recording by a Group or Dance Band | Group | Talk Yur Talk | Trinidad & Tobago | Yes | 2000 |
| 3 Canal | Best Rapso Recording | Group | Talk Yur Talk | Trinidad & Tobago | Yes | 2000 |
| Gypsy | Best Social Commentary | Artist | Soul of the Nation | Trinidad & Tobago | No | 2000 |
| Gypsy | Calypso of the Year | Artist | Soul of the Nation | Trinidad & Tobago | No | 2000 |
| Gypsy | Male Vocalist of the Year | Artist | Soul of the Nation | Trinidad & Tobago | No | 2000 |
| Becket | Best Party Calypso | Artist | Small Pin | St. Vincent and the Grenadines | No | 2000 |
| Frankie McIntosh | Producer of the Year | Producer | Small Pin | St. Vincent and the Grenadines | No | 2000 |
| Frankie McIntosh | Arranger of the Year | Arranger | Small Pin | St. Vincent and the Grenadines | Yes | 2000 |
| Carol Hodge / Curlan | Best Engineered Recording | Engineer | Small Pin | Trinidad & Tobago | No | 2000 |
| Becket | Male Vocalist of the Year | Artist | Small Pin | St. Vincent and the Grenadines | No | 2000 |
| Xtatik | Best Recording by a Group or Dance Band | Band | Showdown | Trinidad & Tobago | No | 2000 |
| The 2001 Sunshine Awards | Sunshine Awards 2001 | Was Cancelled Due To | September 11 Terrorists | Attack On The United States | Yes | 2001 |
| Singing Sandra | Calypso of the Year | Artist | Voices From The Ghetto | Trinidad & Tobago | Yes | 2000 |
| Singing Sandra | Female Vocalist of the Year | Artist | Voices of the Ghetto | Trinidad & Tobago | No | 2000 |
| Singing Sandra | Best Social Commentary | Artist | Voices of the Ghetto | Trinidad & Tobago | Yes | 2000 |
| Red Plastic Bag | Male Vocalist of the Year | Artist | Volcano | Barbados | No | 2000 |
| Red Plastic Bag | Best Party Calypso | Artist | Volcano | Barbados | Yes | 2000 |
| General val | Best Social Commentary | Artist | Unity | St. Thomas USVI | No | 2000 |
| Twiggy | Best Creative Humor | Artist | Up Under Me | Trinidad & Tobago | No | 2000 |
| Andy Narell | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Panist | | USA | Yes | 2000 |
| Sammie C | Best Political Commentary | Artist | Unite Dem Feeding Horse | Antigua | No | 2000 |
| Desperadoes Steel Orchestra | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | The Lord Kitchener Sunshine Award | Trinidad & Tobago Panorama Champions | Trinidad & Tobago | Yes | 2000 |
| Lenox Bobby Mohammed / Jerry Jemott | The SUNSHINE Awards Hall of Fame(TM) | Inductees for Steelband Music | | Trinidad & Tobago | Yes | 2000 |
| Striker (Percy Oblington) / Superior (Andrew Marcano) / Brigo (Samuel Abrahm) | The SUNSHINE Awards Hall of Fame(TM) | Inductees for Calypso Music | | Trinidad & Tobago | Yes | 2000 |
| Peter Pitts | Friend of the Arts SUNSHINE Award | Friend of the Art | | Trinidad & Tobago | Yes | 2000 |
| 3 Canal | The People’s Choice Award | Group | | Trinidad & Tobago | No | 2000 |
| Allison Hinds | Female Vocalist of the Year | Artist | Togetherness | Barbados | Yes | 2000 |
| Nicholas Brancker / Terry Arthur | Best Engineered Recording | Engineer | Togetherness | Barbados / Barbados | Yes | 2000 |
| Nichplas Brancker / Terry Arthur | Arranger of the Year | Arrangers | Togetherness | Barbados | No | 2000 |
| Nicholas Brancker / Terry Arthur | Producer of the Year | Producers | Togetherness | Barbados | Yes | 2000 |
| Square One | Best Party Calypso | Artist | Togetherness | Barbados | No | 2000 |
| Black Prince | Best Creative Humor | Calypsonian | It Done Happen Already | Trinidad & Tobago | No | 2002 |
| Shadow | Best Social Commentary | Calypsonian | HIV | Trinidad & Tobago | Yes | 2002 |
| Margaret Woodroffe | Best Gospelypso Recording by Duo or Group | Gospel Artist | Hold On To Your Family | Trinidad & Tobago | No | 2002 |
| Wayne Rodriguez | Best Social Commentary | Calypsonian | Heroes of A Nation | Trinidad & Tobago | No | 2002 |
| Wayne Rodriguez | Male Vocalist of the Year | Calypsonian | Heroes of A Nation | Trinidad & Tobago | No | 2002 |
| Scrunter & Nikki Crosby | Best Creative Humor | Calypsonian / Comedian | Gimme A Break | Trinidad & Tobago | Yes | 2002 |
| Marilyn Joseph | Best Gospelypso Recording by Duo or Group | Gospel Artist | Gimme Room | Trinidad & Tobago | No | 2002 |
| Pelham Goddard | Arranger of the Year | Arranger | Good News | Trinidad & Tobago | Yes | 2002 |
| Phase 11 Pan Grove | Best Recording by Steelband Orchestra | Steelband Orchestra | Freedom | Trinidad & Tobago | No | 2002 |
| JMC Triveni | Best Chutney-Soca Recording | Chutney Band | Dr. Sampat | Trinidad & Tobago | No | 2002 |
| Rikki Jai | Best Chutney-Soca Recording | Chutney Artist | Dulahin | Trinidad & Tobago | Yes | 2002 |
| Scrunter | Best Soca-Parang Recording | Calypsonian / Arranger | Eat Something | Trinidad & Tobago | Yes | 2002 |
| Nicole Wilson | Best New Female Vocalist | Performing Artist | Declare | Trinidad & Tobago | No | 2002 |
| Nicole Wilson | Best Gospelypso Recording by Duo or Group | Gospel Artist | Declare | Trinidad & Tobago | No | 2002 |
| Traffic Man | Best Soca-Parang Recording | Chutney Artist | Chutney Parang Sweet | Canada | No | 2002 |
| Drupatee | Best Soca-Parang Recording | Chutney Artist | Chutney Parang | Trinidad & Tobago | No | 2002 |
| George Eric Moxey | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Caribbean (Posthumously) | | Bahamas U S V I | Yes | 2002 |
| McClean Emmanuel (Mighty Short Shirt) | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Antigua | Yes | 2002 |
| Exodus | Best Recording by Steelband Soloist | Steelband Orchestra | A Happy Song | Trinidad & Tobago | No | 2002 |
| Neal & Massy Trinidad All Stars | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | The Lord Kitchener Sunshine Award | 2002 Trinidad & Tobago Panorama Champions | Trinidad & Tobago | Yes | 2002 |
| Carl Beaver Henderson | 1998 Journalist Award | Producer | Nah Leaving | Trinidad & Tobago | No | 2002 |
| Carl Beaver Henderson | Producer of the Year | Producer | Nah Leaving | Trinidad & Tobago | No | 2002 |
| Denyse Plummer | Best Social Commentary | Calypsonian | Nah Leaving | Trinidad & Tobago | Yes | 2002 |
| Carl Beaver Henderson | Arranger of the Year | Arranger | Nah Leaving | Trinidad & Tobago | No | 2002 |
| Denyse Plummer | Female Vocalist of the Year | Calypsonian | Nah Leaving | Trinidad & Tobago | No | 2002 |
| Denyse Plummer | Calypso of the Year | Calypsonian | Nah Leaving | Trinidad & Tobago | No | 2002 |
| Burning Flames | Best Recording by a Group or Dance Band | Band | Mud Dung | Antigua | No | 2002 |
| Burning Flames | Best Party Calypso | Band | Mud Dung | Antigua | No | 2002 |
| Shadow | Best Creative Humor | Calypsonian | Looking for Horn | Trinidad & Tobago | No | 2002 |
| Shadow | Calypso of the Year | Calypsonian | Looking For Horn | Trinidad & Tobago | Yes | 2002 |
| CNIO | Best Recording by a Group or Dance Band | Band | Kabhi Aanson | Canada | Yes | 2002 |
| Babla & Kanchan | Best Chutney-Soca Recording | Chutney Artist | Kahe Mare | India | No | 2002 |
| T. C. | Best Party Calypso | Calypsonian | Kim | Barbados | No | 2002 |
| T. C. | Female Vocalist of the Year | Calypsonian | Kim | Barbados | Yes | 2002 |
| T. C. | Calypso of the Year | Calypsonian | Kim | Barbados | No | 2002 |
| Anthony Voisin & elan parle | Best Recording by a Group or Dance Band | Band | Just Another F in Jam | Trinidad & Tobago | Yes | 2002 |
| Luta | Male Vocalist of the Year | Calypsonian | Jamoo Woman | Trinidad & Tobago | No | 2002 |
| Luta | Calypso of the Year | Calypsonian | Jamoo Woman | Trinidad & Tobago | No | 2002 |
| Dobby Dobson | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Reggae Music | | Jamaica West Indies | Yes | 2002 |
| Olive Lewin | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Jamaican Folk Music | | Jamaica West Indies | Yes | 2002 |
| Crazy | Male Vocalist of the Year | Calypsonian | Together | Trinidad & Tobago | Yes | 2002 |
| Shadow | Best Party Calypso | Calypsonian | Stranger | Trinidad & Tobago | Yes | 2002 |
| Skiffle Bunch | Best Recording by Steelband Orchestra | Steelband Orchestra | Stranger | Trinidad & Tobago | Yes | 2002 |
| Winston Bailey (Shadow) / Fitz Melo Thomas / Carl Beaver Henderson | Arranger of the Year | Calypsonian / Arranger | Stranger | Trinidad & Tobago | No | 2002 |
| Winston Baily (Shadow) | Producer of the Year | Calypsonian | Stranger | Trinidad & Tobago | Yes | 2002 |
| Jeff Pelay Elva | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypso Music | | St. Lucia West Indies | Yes | 2002 |
| Ming / elan parle | Producer of the Year | Group | Spirit of Music | Trinidad & Tobago | No | 2002 |
| Ming / elan parle | Arranger of the Year | Arranger | Spirit of Music | Trinidad & Tobago | No | 2002 |
| Candice Alcantara | Female Vocalist of the Year | Performing Artist | Spirit of the Music | Trinidad & Tobago | No | 2002 |
| Candice Alcantara | Best New Female Vocalist | Performing Artist | So Far Away | Trinidad & Tobago | Yes | 2002 |
| Krosfyah | Best Recording by a Group or Dance Band | Band | Sal Pase | Barbados | No | 2002 |
| Krosfyah | Best Party Calypso | Band | Sak Pase | Barbados | No | 2002 |
| Traffic Man | Best Chutney-Soca Recording | Chutney Artist | Ramragee | Canada | No | 2002 |
| Traffic | Best Party Calypso | Band | Party Like We | Trinidad & Tobago | No | 2002 |
| Traffic | Best Recording by a Group or Dance Band | Band | Party Like We | Trinidad & Tobago | No | 2002 |
| Sean Daniel | Best Gospelypso Recording by Duo or Group | Gospel Artist | Numbers | Trinidad & Tobago | Yes | 2002 |
| CNIO | Arranger of the Year | Group | O Mere Dil Ke Chain | Canada | No | 2002 |
| Sean Daniel | Best Social Commentary | Calypsonian | Numbers | Trinidad & Tobago | No | 2002 |
| Sean Daniel | Male Vocalist of the Year | Calypsonian | Numbers | Trinidad & Tobago | No | 2002 |
| Marilyn Joseph | Female Vocalist of the Year | Gospel Artist | No Matter | Trinidad & Tobago | No | 2002 |
| DeFosto | Best Social Commentary | Calypsonian / Performing Artist | Are We The Mecca For True | Trinidad & Tobago | Yes | 2003 |
| Krosfyah | Best Recording by a Group or Dance Band | Dance Band | Action | Barbados | No | 2003 |
| Nicholas Brancker | Arranger of the Year | Arranger | Vegetarian | Barbados | No | 2002 |
| Edwin Yearwood | Male Vocalist of the Year | Calypsonian | Vegetarian | Barbados | No | 2002 |
| Edwin Yearwood | Best Social Commentary | Calypsonian | Vegitarian | Barbados | No | 2002 |
| Desperadoes | Best Recording by Steelband Orchestra | Steelband Orchestra | Yur Looking for Horn | Trinidad & Tobago | No | 2002 |
| Ranjan Ramdass | Producer of the Year | Producer | Ye Dil Mein Rehne Wale | Canada | No | 2002 |
| Square One | Best Recording by a Group or Dance Band | Band | Wine Back | Barbados | No | 2002 |
| Square One | Best Party Calypso | Band | Wine Back | Barbados | No | 2002 |
| Nicholas Branker | Producer of the Year | Producer | Vegetarian | Barbados | No | 2002 |
| Noel Professor Richards | Best Gospelypso Recording by Duo or Group | Gospel Artist | True or Lie | Trinidad & Tobago | No | 2002 |
| Boscoe Holder | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | For Art Choreography Dance Music | | Trinidad & Tobago | Yes | 2002 |
| Sullivan Walker | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Acting | | Trinidad & Tobago | Yes | 2002 |
| Aubrey Adams | Friend of the Arts SUNSHINE Award | Friend of the Arts | | Trinidad & Tobago | Yes | 2002 |
| Garfield Blackman (Ras Shorty I) | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Trinidad & Tobago | Yes | 2002 |
| Clifford Alexis | The SUNSHINE Awards Hall of Fame(TM) | Panist | | Trinidad & Tobago | Yes | 2002 |
| Sonny Francois (Mighty Power) | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Trinidad & Tobago | Yes | 2002 |
| Crazy | Calypso of the Year | Calypsonian | Together | Trinidad & Tobago | No | 2002 |
| Margaret Woodroffe | Best New Female Vocalist | Artist | Tomorrow | Trinidad & Tobago | No | 2002 |
| Crazy | Best Social Commentary | Calypsonian | Together | Trinidad & Tobago | No | 2002 |
| Fay-Ann Lyons | Best Party Calypso | Calypsonian / Performing Artist | My Time Now | Trinidad & Tobago | No | 2003 |
| Preacher | Best Chutney-Soca Recording | Chutner Performing Artist | My Dulahin | Trinidad & Tobago | No | 2003 |
| Heeralal | Best Chutney-Soca Recording | Chutner Performing Artist | Leh We Go To Mayaro | Trinidad & Tobago | No | 2003 |
| Scrunter | Male Vocalist of the Year | Calypsonian / Performing Artist | Jumbie | Trinidad & Tobago | Yes | 2003 |
| Scrunter | Best Party Calypso | Calypsonian / Performing Artist | Jumbie | Trinidad & Tobago | No | 2003 |
| Freddie McGregor | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Performing Artist | | Jamaica | Yes | 2003 |
| Red Plastic Bag | Male Vocalist of the Year | Calypsonian / Performing Artist | In Meh Pants | Barbados | No | 2003 |
| Frantz Voltaire | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Movie Producer | | Haiti | Yes | 2003 |
| Jean Julien | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Historian | | Haiti | Yes | 2003 |
| Tabou Combo | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Haitian band | | Haiti | Yes | 2003 |
| DeFosto | Best Party Calypso | Calypsonian / Performing Artist | Firestorm | Trinidad & Tobago | No | 2003 |
| Singing Althea | Best Social Commentary | Calypsonian / Performing Artist | Exposed | Antigua | No | 2003 |
| Singing Althea | Female Vocalist of the Year | Calypsonian / Performing Artist | Exposed | Antigua | No | 2003 |
| Square One | Best Recording by a Group or Dance Band | Dance Band | Don’t Stop The Carnival | Barbados | No | 2003 |
| Burning Flames | Best Recording by a Group or Dance Band | Dance Band | Children Call Een | Antigua | Yes | 2003 |
| Sanelle Dempter | Female Vocalist of the Year | Calypsonian / Performing Artist | Chances | Trinidad & Tobago | Yes | 2003 |
| Denyse Plummer | Female Vocalist of the Year | Calypsonian / Performing Artist | Cathersis | Trinidad & Tobago | No | 2003 |
| Rupee | Best Party Calypso | Calypsonian / Performing Artist | Blame It On The Music | Barbados | No | 2003 |
| Arturo Tappin | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Musician | | Barbados | Yes | 2003 |
| 3 Canal / Andre Tanker | Best Party Calypso | Calypsonian / Performing Artist | Ben Lion | Trinidad & Tobago | Yes | 2003 |
| The Swingin’ Stars Band | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Musicians | | Dominica | Yes | 2004 |
| Faye Anne Lyons | Calypso of the Year | Calypsonian | Display | Trinidad & Tobago | No | 2004 |
| Timmy | Male Vocalist of the Year | Calypsonian | Bumpa Catcha Fire | Barbados | No | 2004 |
| Paul King Obstinate Richards | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Antigua | Yes | 2004 |
| Allison Hinds | Female Vocalist of the Year | Calypsonian / Performing Artist | Wine Back | Barbados | No | 2003 |
| Kevin Lyttle | Male Vocalist of the Year | Calypsonian / Performing Artist | Turn Me On | Barbados | No | 2003 |
| Lord Creator / Kenrick Randolph Patrick | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Trinidad & Tobago | Yes | 2003 |
| Curtis Anthony Pierre | The SUNSHINE Awards Hall of Fame(TM) | Arranger / Teacher – Steelband Music | | Trinidad & Tobago | Yes | 2003 |
| Vernon Bertie Manette | The SUNSHINE Awards Hall of Fame(TM) | Arranger / Steelband Music | | Trinidad & Tobago | Yes | 2003 |
| Exodus | The Lord Kitchener SUNSHINE Award | Trinidad & Tobago 2003 Panorama Steelband Champions | | Trinidad & Tobago | Yes | 2003 |
| Mighty Caruso / Emmanuel Pierre | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Trinidad & Tobago | Yes | 2003 |
| Mighty Dougla / Clytus Ali | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Trinidad & Tobago | Yes | 2003 |
| Paul Keens-Douglas | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Drama / Comedy | | Trinidad & Tobago | Yes | 2003 |
| Traffic | Best Recording by a Group or Dance Band | Dance Band | Take Yur Time | Trinidad & Tobago | No | 2003 |
| Kenneth Blake | Friend of the Arts SUNSHINE Award | Promoter | | St. Thomas USVI | Yes | 2003 |
| Crazy | Best Social Commentary | Calypsonian / Performing Artist | Shoes | Trinidad & Tobago | No | 2003 |
| Crazy | Male Vocalist of the Year | Calypsonian / Performing Artist | Shoes | Trinidad & Tobago | No | 2003 |
| Rikki Jai & Double D | Best Chutney-Soca Recording | Chutner Performing Artist | Scopian | Trinidad & Tobago | Yes | 2003 |
| Man-Child | Best Social Commentary | Calypsonian / Performing Artist | Now For Now Mentality | Trinidad & Tobago | No | 2003 |
| Fay-Ann Lyons | Female Vocalist of the Year | Calypsonian / Performing Artist | My Time Now | Trinidad & Tobago | No | 2003 |
| Moses Josiah | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Musician | | Guyana | Yes | 2004 |
| Percy Lord Zeigfield Simon | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Grenada | Yes | 2004 |
| Oliver Lord Radio Bromes | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypsonian | | Barbados | Yes | 2005 |
| Leo McDonald Blenman (Mighty Gryner) | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypsonian | | Barbados | Yes | 2005 |
| King T-Mo | Male Vocalist of the Year | Calypsonian | Woman Dezerve the Best | St. Maarten | No | 2004 |
| Connector | Best Social Commentary | Calypsonian | Where Family Values Gone | Canada | No | 2004 |
| Krosfyah | Calypso of the Year | Calypsonian | We Coming | Barbados | No | 2004 |
| Ivan Williams | Friend of the Arts SUNSHINE Award | Promoter | | Trinidad & Tobago | Yes | 2004 |
| Alan Gervais (Posthumously) | The SUNSHINE Awards Hall of Fame(TM) | Pan Tuner | | Trinidad & Tobago | Yes | 2004 |
| Lincoln Noel | The SUNSHINE Awards Hall of Fame(TM) | Pan Tuner | | Trinidad & Tobago | Yes | 2004 |
| David Rudder & Carl Jacobs | Best Social Commentary | Calypsonians | Trini to the Bone | Trinidad & Tobago | Yes | 2004 |
| David Rudder & Carl Jacobs | Calypso of the Year | Calypsonian | Trini to the Bone | Trinidad & Tobago | Yes | 2004 |
| David Rudder & Carl Jacobs | Male Vocalist of the Year | Calypsonians | Trini to the Bone | Trinidad & Tobago | Yes | 2004 |
| Gillo | Best Social Commentary | Calypsonian | Time to Resign | Barbados | No | 2004 |
| Roger George | Best Social Commentary | Calypsonian | These are the Days | Trinidad & Tobago | No | 2004 |
| Aquannette Chinnery | Calypso of the Year | Calypsonian | Sweet | St. Thomas | No | 2004 |
| Edwin Yearwood | Male Vocalist of the Year | Calypsonian | Sorry | Barbados | No | 2004 |
| Barrington Watson | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Painter | | Jamaica | Yes | 2004 |
| Denyse Plummer | Calypso of the Year | Calypsonians | Identity | Trinidad & Tobago | No | 2004 |
| Jean-Jean Pierre | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Musician / Composer | | Haiti | Yes | 2004 |
| Carl Jazzy Pantin | The SUNSHINE Awards Hall of Fame(TM) | Promoter | | Trinidad & Tobago | Yes | 2005 |
| Nathaniel Crichlow | The SUNSHINE Awards Hall of Fame(TM) | Steelban Promoter & Organizer | | Trinidad & Tobago | Yes | 2005 |
| Kelvin Zuzie St. Rose | The SUNSHINE Awards Hall of Fame(TM) | Steelband Tuner | | Trinidad & Tobago | Yes | 2005 |
| Ernest Galloway (Prince Galloway) | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | St. Croix | Yes | 2005 |
| Roger George | Male Vocalist of the Year | Calypsonian | On and On | Trinidad & Tobago | No | 2005 |
| Ginja | Female Vocalist of the Year | Calypsonian | Nice & Slow | Trinidad & Tobago | No | 2005 |
| Tigress | Female Vocalist of the Year | Calypsonian | Literacy | Trinidad & Tobago | No | 2005 |
| Sanelle Dempster | Female Vocalist of the Year | Calypsonian | Little Bit | Trinidad & Tobago | No | 2005 |
| Sanelle Dempster | Calypso of the Year | Calypsonian | Little Bit | Trinidad & Tobago | No | 2005 |
| Tony Prescott | Male Vocalist of the Year | Calypsonian | Mash | Trinidad & Tobago | No | 2005 |
| Edwin Yearwood | Male Vocalist of the Year | Calypsonian | Keep it Rollong | Barbados | No | 2005 |
| Square One | Calypso of the Year | Calypsonian | Just Wait | Barbados | No | 2005 |
| Ernest Ranglin | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Musician / Composer | | Jamaica | Yes | 2005 |
| Cyril Shaw | Friend of the Arts SUNSHINE Award | Promoter | | Guyana | Yes | 2005 |
| Habeeb Khan | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Comedian | | Guyana | Yes | 2005 |
| Michelle Sylvester | Female Vocalist of the Year | Calypsonian | Go Ahead | Trinidad & Tobago | Yes | 2005 |
| Faye Anne Lyons | Female Vocalist of the Year | Calypsonian | Freedom | Trinidad & Tobago | No | 2005 |
| Faye Anne Lyons | Calypso of the Year | Calypsonian | Freedom | Trinidad & Tobago | No | 2005 |
| Sherwayne Winchester | Male Vocalist of the Year | Calypsonian | De Band Coming | Trinidad & Tobago | Yes | 2005 |
| Shurwayne Winchester | Calypso of the Year | Calypsonian | De Band Coming | Trinidad & Tobago | Yes | 2005 |
| Lord Panama ( George Allen) | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypsonian | | Panama | Yes | 2007 |
| Rex Nettleford | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Dance | | Jamaica West Indies | Yes | 2007 |
| Monty Alexander | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Musician | | Jamaica West Indies | Yes | 2007 |
| Emeline Michel | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Performing Artist – Music | | Haiti | Yes | 2007 |
| Hugh Sam | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Musician Composer Arranger | | Guyana | Yes | 2007 |
| Shirley Robinson | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Music Teacher | | Grenada West Indies | Yes | 2007 |
| Andrew Beddoe | The SUNSHINE Awards Hall of Fame(TM) | For Steelband Music | | Trinidad & Tobago | Yes | 2006 |
| Orville Duncan | The SUNSHINE Awards Hall of Fame(TM) | For Steelband Music | | Trinidad & Tobago | Yes | 2006 |
| Prince Cumberbatch | Friend of the Arts SUNSHINE Award | Friend of the Arts | | Trinidad & Tobago | Yes | 2006 |
| John Arnold – Director of Signal Hill Alumni Choir of Tobago | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Special Award for Music & Dance | | Trinidad & Tobago | Yes | 2006 |
| The Mighty Duke (Kelvin Pope) | The SUNSHINE Awards Hall of Fame(TM) | For Calypso Music | | Trinidad & Tobago | Yes | 2006 |
| Lord Nelson (Robert Nelson) | The SUNSHINE Awards Hall of Fame(TM) | For Calypso Music | | Trinidad & Tobago | Yes | 2006 |
| Creighton Pencheon | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Special Award for contribution to Caribbean culture | | St Kitts West Indies | Yes | 2006 |
| Dr. Marcia Keizs-President of York College of the City University of New York | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Special Award for Education | | Jamaica West Indies | Yes | 2006 |
| Keith Maxwell Proctot | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Special Award for Contribution to Caribbean Music | | Guyana | Yes | 2006 |
| The Mighty Sparrow (Dr. Slinger Francisco) | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Heritage Award – For 51 Years of Performing Calypso | First Calypso – Jean & Dinah | Trinidad & Tobago | Yes | 2006 |
| Irving Burgie – Author of Barbados National Anthem | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Song of the Century Award | DAY-O | USA | Yes | 2006 |
| 3 canal | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | | | | No | 2005 |
| Kevin Lyttle | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypsonian | Turn Me On | St. Vincent and the Grenadines | Yes | 2005 |
| Bernadette Scott & Love Movement | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Dance Group | | Trinidad & Tobago | Yes | 2005 |
| Elwin McQuilkin – The Black Wizard | SUNSHINE Award Contribution to Calypso Music | Calypsonian | | Grenada | Yes | 2009 |
| Eulalia Bernard | SUNSHINE Award Contribution to Science & Eduacation | Writer Poet Educator | | Costa Rica | Yes | 2009 |
| Habib Kagimu | The SUNSHINE Award for Humanitarian Services | Philanthropist | | Uganda Africa | Yes | 2008 |
| Leroy Clarke | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Leroy Clarke (Artist) | | Trinidad & Tobago | Yes | 2008 |
| Sundar Popo (posthumously) | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Chutney-soca Performing Artist | | Trinidad & Tobago | Yes | 2008 |
| Holly Betaudier | Friend of the Arts SUNSHINE Award | Promoter – The Mighty Sparrow SUNSHINE Award | | Trinidad & Tobago | Yes | 2008 |
| Belgrave Bonaparte (posthumously) | The SUNSHINE Awards Hall of Fame(TM) | Steelband Music | | Trinidad & Tobago | Yes | 2008 |
| John Ernesto Ferreira | The SUNSHINE Awards Hall of Fame(TM) | Steelband Music | | Trinidad & Tobago | Yes | 2008 |
| Quintyn Toby Joseph (The Mighty Toiler) | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Calypsonian | | St Vincent & the Grenadines | Yes | 2008 |
| Robert Stafford (The Mighty Skipper) | The SUNSHINE Awards Hall of Fame(TM) | Calypso Music | | St. Croix USVI | Yes | 2008 |
| Oliver Samuel | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Comedian | | Jamaica WI | Yes | 2008 |
| Mamadou Dahoue | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | African Dancer | | Ivory Coast Africa | Yes | 2008 |
| CCH Pounder (Carol Christine Pounder-Kone) – The Irving Burgie SUNSHINE Award | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Actress | | Guyana | Yes | 2008 |
| Lauren Ramdhanny | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Music Teacher | | Grenada West Indies | Yes | 2008 |
| Rupert Philo (King Swallow) | The SUNSHINE Awards Hall of Fame(TM) | Calypso Music | | Antigua & Barbuda | Yes | 2008 |
| Leroy Calliste (Black Stalin) | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Trinidad & Tobago | Yes | 2007 |
| Fred Mitchell (Mighty Composer) | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Trinidad & Tobago | Yes | 2007 |
| Francis Wickham | The SUNSHINE Awards Hall of Fame(TM) | Steelband Arranger | | Trinidad & Tobago | Yes | 2007 |
| Earl Rodney | The SUNSHINE Awards Hall of Fame(TM) | Steelband Arranger | | Trinidad & Tobago | Yes | 2007 |
| Don Bobb | The SUNSHINE Award for Contribution to Caribbean Art Comedy Dance Drama Music and Poetry | Journalist | | St. Vincent and the Grenadines | Yes | 2007 |
| Sidiki Conde | African Dance | Dancer | | Guinea West Africa | Yes | 2011 |
| Winston Fleary | Caribbean & African Dance | Dancer | | Carriacou | Yes | 2011 |
| Aubrey Lacu Samuel | Contribution to Steelband Music | Musician | | Antigua | Yes | 2011 |
| Norman Darway Adams | SUNSHINE Awards Hall of Fame | Player Agent Storyteller Researcher Writer Radio and Television Host and above all Lecturer/ hHstorian. | | Trinidad & Tobago | Yes | 2010 |
| Yves Joseph | Contribution to Humanity | Performing Artist Song writer Producer | | Haiti | Yes | 2010 |
| Drupatee Persad | Performing Arts – contribution to Chutney music. | Performing Artist | | Trinidad & Tobago | Yes | 2010 |
| Bill Trotman | SUNSHINE Awards Hall of Fame | Comedian | | Trinidad & Tobago | Yes | 2010 |
| The Tradewinds | SUNSHINE Awards Hall of Fame | Musicians | The original members of the Tradewinds are Dave Martins Clive Rosteing Harry Cupid Jeff Japal and Richard Terry. Terry Dyal performed with the band from 1969 to 1981 and Joe Brown performed from 1968 to 1978. Other members who are now deceased are the ori | Canada, Guyana, Virgin Islands | Yes | 2010 |
| Famoro Dioubate | Performing Arts – African Music | Musician | | Guinea West Africa | Yes | 2010 |
| Sonny Blacks | Friend of the Arts SUNSHINE Award | Promoter | | England | Yes | 2010 |
| Ramiro Crawford | Contribution to the Performing Arts and Journalism. | Journalist & Promoter | | Costa Rica | yes | 2010 |
| Dancin Africa | Performing Arts – traditional and contemporary African Caribbean folk calypso street and modern jazz and Hip Hop | Dancin Africa Dance Troupe | | Barbados | Yes | 2010 |
| Rwangyezi Stephen & The Ndere Dance Troupe | SUNSHINE Award Contribution to African Dance | Director African Dance | | Uganda Africa | Yes | 2009 |
| Frank and Claude Martineau | SUNSHINE Awards Friend of the Arts | Promoters of the Performing Arts | | Trinidad & Tobago | Yes | 2009 |
| Anthony Emrold Phillip – Brother Valentino | The SUNSHINE Awards Hall of Fame(TM) | Calypsonian | | Trinidad & Tobago | Yes | 2009 |
| Bernard Butch Kelman | The SUNSHINE Awards Hall of Fame(TM) | Steelband Tuner | | Trinidad & Tobago | Yes | 2009 |
| Alston Becket Cyrus | SUNSHINE Award Contribution to Calypso Music | Calypsonian | | St. Vincent & The Grenadines | Yes | 2009 |
| Armando Savaranga Crisanto | SUNSHINE Award Contribution to African Dance | Choreographer Dance Teacher | | Honduras | Yes | 2009 |
| Dr. Ulric Gibson | SUNSHINE Award Contribution to Science & Eduacation | Public Health Professor | | Guyana | Yes | 2009 |
| William Elcock — Scaramouch | SUNSHINE Award Contribution to Calypso Music | Calypsonian | | Grenada | Yes | 2009 |
| Merle AlbinoDeCoteau | Hall of Fame | Music Teacher | | Trinidad & Tobago | Yes | 2012 |
| Clifton Lewis | Hall of Fame | Performing Artist | | Trinidad & Tobago | Yes | 2012 |
| Keshorn Walcott | Excellence in Sports | 2012 Olympic Gold Medalist | | Trinidad & Tobago | Yes | 2012 |
| Monty Alexander | Lifetime Achievement Award | Performing Artist | | Jamaica | Yes | 2012 |
| Gina Faustin | Contribution to Haitian Culture | Television Personality | | Haiti | Yes | 2012 |
| Malcolm Corrica | Hall of Fame | Performing Artist | | Guyana | Yes | 2012 |
| Martin Vejarano | Contribution to Columbian Culture | Performing Artist | | Colombia | Yes | 2012 |
| Dr Prince Ramsey | Friend of the Arts SUNSHINE Award | Music Producer | | Antigua | Yes | 2012 |
| Rawdon Edwards | Contribution to the Performing Arts | Performing Artist | | Antigua | Yes | 2012 |
| Patrick Arnold | SUNSHINE Awards Hall of Fame | | | Trinidad & Tobago | Yes | 2011 |
| James Delia | Contribution to Humanity – Haiti | Attorney | | United States of America | Yes | 2011 |
| Verne Hodge | SUNSHINE Awards Hall of Fame | United States Judge | | United States Virgin Islands | Yes | 2011 |
| Dr Eric Williams | Friend of the Arts SUNSHINE Award | Contribution to the Performing Arts | | Trinidad & Tobago | Yes | 2011 |
| John Buddy Williams | SUNSHINE Awards Hall of Fame | Musician | | Trinidad & Tobago | Yes | 2011 |
| Ortniel Bacchus | SUNSHINE Awards Hall of Fame | Calypsonian – Tobago Crusoe | | Trinidad & Tobago | Yes | 2011 |
| Cyril Diaz | SUNSHINE Awards Hall of Fame | Musician | | Trinidad & Tobago | Yes | 2011 |
| Edward Teddy Pinheir | Friend of the Arts SUNSHINE Award | Researcher/Historian | | Trinidad & Tobago | Yes | 2011 |
| William Munro | Friend of the Arts SUNSHINE Award | Promoter | | Trinidad & Tobago | Yes | 2011 |
| Mungal Patasar | Contribution to Caribbean Music | Musician | | Trinidad & Tobago | Yes | 2011 |
| Rudy Bishop | Contribution to Steelband Music | Musican | | Guyana | Yes | 2011 |
| Jit Samaroo | Hall of Fame | Steelpan Arranger | | Trinidad & Tobago | Yes | 2013 |
| Ray Holman | Hall of Fame | Steelpan Arranger | | Trinidad & Tobago | Yes | 2013 |
| Dr Hollis Liverpool | 25 Years of Service | Co-Founder SUNSHINE Awards Hall of Fame | | Trinidad & Tobago | Yes | 2013 |
| Janice Forde | 25 Years of Service | Talent Co-ordinator | | Trinidad & Tobago | Yes | 2013 |
| Joseph (Joe) Brown | 25 Years of Service | Musical Director | | Trinidad & Tobago | Yes | 2013 |
| Von Martin | Friend of the Arts SUNSHINE Award | Radio Broadcaster/Producer | | Trinidad & Tobago | Yes | 2013 |
| Fitzroy Coleman | Hall of Fame | Musician | | Trinidad & Tobago | Yes | 2013 |
| Roy Cape | Hall of Fame | Musician | | Trinidad & Tobago | Yes | 2013 |
| Errol Ince | Hall of Fame | Musician/Producer/Song writer | | Trinidad & Tobago | Yes | 2013 |
| Dr. Jacob D. Elder | Contribution to Culture | Posthumously | | Trinidad & Tobago | Yes | 2013 |
| Rawle Axeback Titus | Contribution to the Performing Arts | Historian/Performer/Researcher | | Trinidad & Tobago | Yes | 2013 |
| Lionel Mitchell | Contribution to Culture | Anthropologist/Author/Teacher | | Trinidad & Tobago | Yes | 2013 |
| Dr. Hans Geiser | 25 Years of Service | SUNSHINE Awards Organization Board Member | | Switzerland | Yes | 2013 |
| Elsie Saint Louis | Contribution to Humanity | Haitian American United for Progress | | Haiti | Yes | 2013 |
| Makerere University | Research and Science | | | Unganda Africa | Yes | 2012 |
| Bob/Wanda Dickerson | African Dance & African Culture | Founders of Universal African Dance & Drum Ensemble | | USA / Africa | Yes | 2012 |
| Dr. Brinsley Samaroo | Dr. Basil Matthews SUNSHINE Award for contribution to education | Professor | | Trinidad & Tobago | Yes | 2012 |
| Randolph St. Louis | Hall of Fame | Steelband Musician | | Trinidad & Tobago | Yes | 2012 |
| Bert Innis-Deceased | Hall of Fame | Musician | | Trinidad & Tobago | Yes | 2012 |
| Paul Noel | Hall of Fame | Performing Artist | | Trinidad & Tobago | Yes | 2012 |
| Erna Letemps | Performing Arts | Haitian Music | | Haiti | Yes | 2015 |
| Godfrey Augustine | Performing Arts | Friend of the Arts | | Grenada | Yes | 2015 |
| Russell Audley Ferdinand Russ” Henderson (Posthumously)””ussell Audley Ferdinand “Russ”””ssell | SUNSHINE Awards Hall of Fame | Arts & Culture – Promoter | | Europe/Trinidad & Tobago | Yes | 2015 |
| Rudy Two Left” Smith””udy “Two Left” “”dy “Two Le””y “Two”” “T | SUNSHINE Awards Hall of Fame | Performing Arts – Steel Band Music | | Europe/Trinidad & Tobago | Yes | 2015 |
| Dr. Alister Francis (Posthumously) | The Dom Basil Matthews SUNSHINE Award | Education | | Antigua & Barbuda | Yes | 2015 |
| Joycelyne Mayas | Contribution to Humanity | | | Haiti | Yes | 2014 |
| Sister Rosario Hackshaw | Contribution to Education & Humanity | | | Trinidad & Tobago | Yes | 2014 |
| National Staffing Associates | SUNSHINE Awards Corporate Award | | | United States | Yes | 2014 |
| Winston Bailey-The Mighty Shadow | SUNSHINE Awards Hall of Fame | Calypso Music | | Trinidad & Tobago | Yes | 2014 |
| Lancelot Layne – (Deceased) | SUNSHINE Awards Hall of Fame | Rapso Music | | Trinidad & Tobago | Yes | 2014 |
| The National Action Cultural Committee | Friend of the Arts SUNSHINE Award | Calypso & Steelband Music | | Trinidad & Tobago | Yes | 2014 |
| Liam Teague | Contribution to Education & the Performing Arts | Steelband Music | | Trinidad & Tobago | Yes | 2014 |
| Hillary Baga” Rezende””illary “Baga”””llary | SUNSHINE Awards Hall of Fame | Steelband Music | | Trinidad & Tobago | Yes | 2014 |
| Orlando Marin | Contribution to the Performing Arts | Latin Music | | Puerto Rico | Yes | 2014 |
| Dheeraj Gayaram | Contribution to the Performing Arts & Indian Culture | Indian Dance & Culture | | Guyana | Yes | 2014 |
| Cecil Ward | SUNSHINE Awards Hall of Fame | Steelband Music | | Barbados | Yes | 2014 |
| Feraba Dance Co. | African Rhythm and Dance | | | West Africa | yes | 2013 |
| Morgianna Varricchio | Contribution to the Performing Arts | | | North Africa | Yes | 2013 |
| Jancy Ball | 25 Years of Service | Stage Manager | | United States | Yes | 2013 |
| Dr. Clement London | Dr. Basil Matthews SUNSHINE Award | Professor Emeritus | | Trinidad & Tobago | Yes | 2013 |
| David Cuffy | SUNSHINE Award | Journalism | | Trinidad & Tobago | Yes | 2016 |
| Holly Betaudier (Posthumously) | SUNSHINE Awards Hall of Fame | Performing Arts | | Trinidad & Tobago | Yes | 2016 |
| Professor Kenneth Julien | Dom Basil Matthews SUNSHINE Award | Education & National Development | | Trinidad & Tobago | Yes | 2016 |
| McCartha Lewis (Calypso Rose) | SUNSHINE Awards Hall of Fame | Calypso Music | | Trinidad & Tobago | Yes | 2016 |
| Aldwin Albino | SUNSHINE Awards Hall of Fame | Calypso & Steelband Music | | Trinidad & Tobago | Yes | 2016 |
| Willard Harris (Lord Relator) | SUNSHINE Awards Hall of Fame | Calypso Music | | Trinidad & Tobago | Yes | 2016 |
| Len Boogsie” Sharpe””en “Boogsie” Sh””n “Boogsie””” “Boogsi”””Boogs””Boogs | SUNSHINE Awards Hall of Fame | Steelband Music | | Trinidad & Tobago | Yes | 2016 |
| Pascual & Gema Forteza | Performing Arts | Classical & Latin Music | | Spain | Yes | 2016 |
| Samir Chatterjee | SUNSHINE Award | Indian Music | | India | Yes | 2016 |
| Eddy Bourjolly | Performing Arts | Jazz & Haitian Music | | Haiti | Yes | 2016 |
| Lance Gibbs | SUNSHINE Award | Sports – Cricket | | Guyana | Yes | 2016 |
| Caldwell Taylor | SUNSHINE Award | Education & Research | | Grenada/Canada | Yes | 2016 |
| Len Smooth” Edwards””en “Smooth” Edw””n “Smooth” “” “Smooth”””Smoot””Smoot | SUNSHINE Awards Hall of Fame | Performing Arts – Steel Band Music | | Trinidad & Tobago | Yes | 2015 |
| Winsford Joker” deVines””insford “Joker””nsfor | SUNSHINE Awards Hall of Fame | Performing Arts – Songwriter | | Trinidad & Tobago | Yes | 2015 |
| Pelham Goddard | Performing Arts | Musician | | Trinidad & Tobago | Yes | 2015 |
| Peter Blood | Performing Arts | Journalism | | Trinidad & Tobago | Yes | 2015 |
| Frankie McIntosh | SUNSHINE Awards Hall of Fame | Contribution to the Performing Arts | | St. Vincent & The Grenadines | Yes | 2015 |
| Sharlene Flores | Performing Arts | Latin/Parang Music | n/a | Trinidad & Tobago | Yes | 2015 |
| Rawle Gibbons | Performing Arts | Research/Dramatist | n/a | Trinidad & Tobago | Yes | 2015 |
| David & Chandrakantha Courtney | Performing Arts | Indian Music | | India/United States | Yes | 2015 |
| Timothee van-Heyningen | Performing Arts | Performing Arts – Music | | St. Maarten | Yes | 2019 |
| Dr Erold Hinds | Performing Arts | Friend of the Arts | | Barbados | Yes | 2019 |
| Robert Amar | Performing Arts | Friend of the Arts | | Trinidad & Tobago | Yes | 2019 |
| Johnny Thomas | Performing Arts | Friend of the Arts | | Trinidad & Tobago | Yes | 2019 |
| Alfred Mayer | SUNSHINE Awards Hall of Fame | A steelband pioneer of the 1940s | | Trinidad & Tobago | Yes | 2019 |
| Darryl Farmer Nappy Henry | Performing Arts | Performing Arts – Music | | Trinidad & Tobago | Yes | 2019 |
| Stedson Red Plastic Bag Wiltshire | Hall of Fame | Performing Arts – Music | | Barbados | Yes | 2019 |
| Dr Gladys West | Education & Technology | Education & Technology | | United States | Yes | 2019 |
| Dr. Andre Cropper | Education & Technology | Education & Technology | | Trinidad & Tobago | Yes | 2019 |
| Jean Appolon | Performing Arts | Haitian Contemporary Dance | | Haiti | Yes | 2019 |
| Albert Laveau | Hall of Fame | Performing Arts – Drama | | Trinidad & Tobago | Yes | 2019 |
| Dr Eugene Novotney | Performing Arts | Steelbannd Music | | USA | Yes | 2017 |
| Miguel del Aguila | Performing Arts | Music | | Uruguay | Yes | 2017 |
| Sandra Andria DeVignes-Millington – Singing Sandra | Performing Arts | Calypso Music | | Trinidad & Tobago | Yes | 2017 |
| Charles Dougherty | Performing Arts | Music | | Jamaica | Yes | 2017 |
| Elio Villafranca | The Performing Arts | Music | | Cuba | Yes | 2017 |
| Pooja Harang | Performing Arts | Dance | | Canada / India | Yes | 2017 |
| Adriano Santos | Performing Arts | Music | | Brazil | Yes | 2017 |
| Canute Spencer | Friend of the Arts SUNSHINE Award | | | Trinidad & Tobago | Yes | 2016 |
| Earl Crosby (Posthumously) | Friend of the Arts SUNSHINE Award | | | Trinidad & Tobago | Yes | 2016 |
