| | | |
| YEAR | AGE CATEGORY | GENRE | NAME |
| 1986 | | CALYPSO | Richard ‘Little Richie’ Holder |
| 1987 | | CALYPSO | Russell ‘Russell D’ Davis |
| 1988 | | CALYPSO | Richard ‘Little Richie’ Holder |
| 1989 | | CALYPSO | Kerry ‘Turbo’ Maxwell |
| 1990 | | CALYPSO | Russell ‘Russell D’ Davis |
| 1991 | | CALYPSO | Russell ‘Russell D’ Davis |
| 1992 | | CALYPSO | Keisha ‘Keisha’ Christian |
| 1993 | | CALYPSO | Keisha ‘Keisha’ Christian |
| 1994 | | CALYPSO | Malika ‘Malika’ Hart |
| 1995 | 8-11 | CALYPSO | Shaka ‘Tiny’ Clarke |
| 1995 | 12-18 | CALYPSO | Elliott ‘Soca Surfer’ Barrow |
| 1996 | 8-11 | CALYPSO | Fabian ‘Fabby’ Odle |
| 1996 | 12-18 | CALYPSO | Malika ‘Malika’ Hart |
| 1997 | 8-11 | CALYPSO | Fabian ‘Fabby’ Odle |
| 1997 | 12-18 | CALYPSO | Tamara ‘Starlight’ Williams |
| 1998 | 12-18 | CALYPSO | Khiomal ‘Khiomal’ Nurse |
| 1999 | 12-18 | CALYPSO | Malika ‘Malika’ Hart |
| 2008 | 13-18 | CALYPSO | Chad “Sir Ruel” Bowen |
| 2009 | 8-12 | CALYPSO | Johari “Dazzle” Taitt |
| 2010 | 8-12 | CALYPSO | Miles “Miles-Z” Gittens |
| 2010 | 8-12 | CALYPSO | Jazz “Jazz-Z” Gittens |
| 2010 | 13-18 | CALYPSO | Aziza “Lil Az” Clarke |
| 2011 | 8-12 | CALYPSO | Carrie-Lyn “Carrie G” Grazette |
| 2011 | 13-18 | CALYPSO | Samantha “Sammy G” Greaves |
| 2012 | 8-12 | CALYPSO | Jazz “Jazz-Z” Gittens |
| 2012 | 13-18 | CALYPSO | Aisha “Mandisa” Butcher |
| 2013 | 8-12 | CALYPSO | Quinn “Quinn P” Prescott |
| 2013 | 13-18 | CALYPSO | Charice “Honesty” Walrond |
| 2014 | 8-12 | CALYPSO | Raanan “Raanan” Hackett |
| 2014 | 13-18 | CALYPSO | Samantha “Sammy G” Greaves |
| 2015 | 8-12 | CALYPSO | Asher “Dynamo” Murrell |
| 2015 | 13-18 | CALYPSO | Adelah “AH-DEE-LAH” Payne |
| 2016 | 8-12 | CALYPSO | Summa ‘Summa’ Sargeant |
| 2016 | 13-18 | CALYPSO | Chad “De Mc” Montiplasir |
| 2017 | 8-12 | CALYPSO | Kiara Carrington |
| 2017 | 13-18 | CALYPSO | Teri “Sparkle-T” Williams-Niles |
| 2018 | 8-12 | CALYPSO | Emari “Browne Star” Browne |
| 2018 | 13-18 | CALYPSO | Dequon “Quon” Alleyne |
| 2019 | 6-10 | CALYPSO | Kenaz "The Mighty Bit Bit" Walker |
| 2019 | 11-14 | CALYPSO | Shontae"Shontae" Alleyne-Clarke |
| 2019 | 15-18 | CALYPSO | Dequon “Quon” Alleyne |
| 2020 | | | NO COMPETITION |
| 2021 | | | NO COMPETITION |
| 2022 | | SOCA | Shontae "Tae" Alleyne-Clarke |
| 2022 | | CALYPSO | Yahandje "Yahandje" Daniel |
| 2023 | | CALYPSO | Shontae "Tae" Alleyne-Clarke |
| 2023 | | SOCA | Sakarah ‘Sakarah’ Thomas |
