• Caribbean Cup
• 2020 2016 2014 2012 2010 Martinique 2008 Jamaica 2007 Trinidad and Tobago 2005 Barbados 2001 Trinidad and Tobago 1999 Trinidad and Tobago 1998 Jamaica / Trinidad and Tobago 1997 Antigua & Barbuda / St. Kitts 1996 Trinidad and Tobago 1995 Cayman Islands/Jamaica 1994 Trinidad and Tobago 1993 Jamaica 1992 Trinidad and Tobago 1991 Jamaica 1990 Trinidad and Tobago 1989 Barbados
• Final 3rd Place Final Group Stage 2nd Round 1st Round Preliminary Round
• Todos Group 3 Group 4 Group 5 Group 6
• Jornada  
• 1 2 3

Group 4

Jogos

Jornada 1 2014-09-04 Guiana Francesa 1-1 Grenada Puerto Rico 2-2 Curaçau

Group 5

Jogos

Jornada 1 2014-09-04 Dominican Rep 0-1 St. Vincent A. e Barbuda 6-0 Anguilla

Group 6

Jogos

Jornada 1 2014-09-03 Dominica 0-0 Guiana St. Kitts 0-0 St. Lucia

Group 3

Jogos

Jornada 1 2014-09-04 Barbados 1-1 Suriname Martinique 6-0 Bonaire