| Performer | Country | Song | Year |
| No Competition | 2011 | ||
| Ricky T | Saint Lucia | “Cwa Stop It” | 2010 |
| Ricky T | Saint Lucia | “Like a Jumbie” | 2009 |
| Ricky T | Saint Lucia | “Wheel & Come Again” | 2008 |
| Ninja Dan | Saint Lucia | “Rise” | 2007 |
| Mista Vybe | Trinidad & Tobago | “Ting for the Road” | 2006 |
| Oronde “Bomani” Charles | St. Vincent | “Who Am I” | 2005 |
| Mantius Cazabon | Saint Lucia | “We Making Love” | 2004 |
| Mantius Cazabon | Saint Lucia | “I Doing A Ting” | 2003 |
| David “Pung Wa” Patrick | St. Kitts-Nevis | “Pussy & Tony” | 2002 |
| Godfrey Dublin | St. Vincent & the Grenadines | “To Take Away” | 2001 |
