Caribbean Cup

Won (16)

2001 2001 Trinidad and Tobago 1999 Trinidad and Tobago 1999 1997 1997 Antigua & Barbuda / St. Kitts 1996 1996 Trinidad and Tobago 1995 1995 Cayman Islands/Jamaica 1994 1994 Trinidad and Tobago 1992 1992 Trinidad and Tobago 1989 Barbados 1989

Runner-up (10)

2014 Jamaica 2014 2012 Antigua and Barbuda 2012 2007 2007 Trinidad and Tobago 1998 1998 Jamaica / Trinidad and Tobago 1991 1991 Jamaica