Starting from an early stage is crucial, hence the Junior Calypso Winners throughout carnival history
| Year | Sobriquet | Name |
| 1972 | Explorer | Leon Lewis |
| 1973 | Singing Fancy | |
| 1974 | Deceiver/La Tumba | |
| 1975 | Explorer | Leon Lewis |
| 1976 | No Competition | |
| 1977 | Styles | Fitzmore Harris |
| 1978 | Solo | Vernon Benjamin |
| 1979 | DJ Nimble | Limbert Carr |
| 1980 | Flat Nose | Stanley Carr |
| 1981 | Douglas | Edmund Dowdie |
| 1982 | Mighty Calypso | Erimore Francis |
| 1983 | Super | Dale Drew |
| 1984 | Tony | Tony George |
| 1985 | Tony | Tony George |
| 1986 | Belto | Craig Lewis |
| 1987 | Smarty Jr. | Ira Harvey |
| 1988 | Young Lion | Dave Brann |
| 1989 | Belto | Craig Lewis |
| 1990 | Young Destroyer | Leston Jacobs |
| 1991 | Kesta | Kester Joseph |
| 1992 | Kesta | Kester Joseph |
| 1993 | Young Destroyer | Leston Jacobs |
| 1994 | King Spider | Hugh James |
| 1995 | Charmer | Amid Browne |
| 1996 | Young Destroyer | Leston Jacobs |
| 1997 | Young Destroyer | Leston Jacobs |
| 1998 | Lady Ferguson | Kenica Samuel |
| 1999 | Buxy | Romeo Dean |
| 2000 | Lady Challenger | Kereeta Farrell |
| 2001 | Lady Challenger | Kereeta Farrell |
| 2002 | Lady Challenger | Kereeta Farrell |
| 2003 | Princess Thalie De Bear |
Thalie King Kethroy Morison |
| 2004 | Princess Thalia Butterfly |
Thalie King Javan Henry |
| 2005 | A’Shante O’ Keiffe Trevoughn Weston |
Princess A’Shante (5-12) Trek (12-19) |
| 2006 | Trevaughn Weston Melinda Gregory |
Lyrics Man (12-19) Singing Holly (5-12) |
| 2007 | Trevaughn Weston A’Shante O’Keiffe |
De Lyricks Man (12-19) A’Shante (5-12) |
| 2008 | Na’im Hurst Rhone Kirby |
The Mighty Hawk (12-19) Mystic Rohne (5-12) |
| 2009 | Colin Beazer Kelsie Watkins |
The Might Tenor (12-19) Youth Crisis (5-12) |
| 2010 | Singing Princess (12-19) Lady Bop (5-12) |
|
| 2011 | ||
| 2012 | ||
| 2013 | ||
| 2014 | ||
| 2015 | ||
| 2016 | ||
| 2017 | Kid Vicious (12-19) Baby Eve (5-12) |
|
| 2018 | King Vicious (12-19) Ge'eve (5-12) |
|
| 2019 |
