• 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 1 Group 2
• Jornada  
• 1 2 3

Group 1

Jogos

Jornada 1 2014-05-31 Montserrat 1-0 USVI

Group 2

Jogos

Jornada 1 2014-05-30 Guiana Francesa 6-0 British VI Aruba 1-0 Turks & Caicos