Awards
| Year | Most Valuable player | Top Goalscorer(Finals only) | Best goalkeeper | Fair play award |
|---|---|---|---|---|
| 1989 | Steve Mark | Dwight Yorke & Philbert Jones (2 goals) | Grenada | |
| 1991 | Paul Davis | Paul Davis (5 goals) | ||
| 1992 | Leonson Lewis (7 goals) | |||
| 1993 | Walter Boyd | Jean Michel Modestin (5 goals) | Saint Kitts and Nevis | |
| 1994 | David Nakhid | |||
| 1995 | David Nakhid | |||
| 1996 | Russell Latapy (6 goals) | |||
| 1997 | Jerren Nixon | Clayton Ince | ||
| 1998 | Stern John | Stern John (10 goals) | Clayton Ince | |
| 1999 | Raciel Martínez | Ariel Álvarez (5 goals) | Clayton Ince | |
| 2001 | Dennis Lawrence | Golman Pierre (5 goals) | Clayton Ince | |
| 2005 | Andy Williams | Luton Shelton (9 goals) | ||
| 2007 | Pierre Richard Bruny | Gary Glasgow (6 goals) | ||
| 2008 | Eric Vernan | Kithson Bain & Luton Shelton (5 goals) | ||
| 2010 | Rodolph Austin | Dane Richards & Kithson Bain (3 goals) | ||
| 2012 |
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