| 2017-06-25 |  Jamaicav CuraçaoCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 2017-06-22 | Jamaicav French GuianaCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |
| 2014-11-18 | Jamaicav Trinidad and TobagoCFU Caribbean Cup | 0–0 | CFU Caribbean Cup |
| 2012-12-12 | Jamaicav CubaCFU Caribbean Cup | 0–1 | CFU Caribbean Cup |
| 2012-12-10 | Jamaicav MartiniqueCFU Caribbean Cup | 0–0 | CFU Caribbean Cup |
| 2012-12-08 | JamaicavFrench GuianaCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 2010-12-05 |  GuadeloupevJamaicaCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |
| 2010-12-03 | Jamaicav GrenadaCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 2010-12-01 |  GuyanavJamaicaCFU Caribbean Cup | 0–4 | CFU Caribbean Cup |
| 2010-11-29 | GuadeloupevJamaicaCFU Caribbean Cup | 0–2 | CFU Caribbean Cup |
| 2010-11-27 | Jamaicav Antigua and BarbudaCFU Caribbean Cup | 3–1 | CFU Caribbean Cup |
| 2008-12-14 | JamaicavGrenadaCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 2008-12-11 | JamaicavGuadeloupeCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 2008-12-07 | JamaicavTrinidad and TobagoCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |
| 2008-12-05 | JamaicavGrenadaCFU Caribbean Cup | 4–0 | CFU Caribbean Cup |
| 2008-12-03 | Jamaicav BarbadosCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 2005-02-24 | CubavJamaicaCFU Caribbean Cup | 0–1 | CFU Caribbean Cup |
| 2005-02-22 | BarbadosvJamaicaCFU Caribbean Cup | 0–1 | CFU Caribbean Cup |
| 2005-02-20 | JamaicavTrinidad and TobagoCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 2001-05-19 | BarbadosvJamaicaCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 2001-05-17 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 2001-05-15 | MartiniquevJamaicaCFU Caribbean Cup | 0–1 | CFU Caribbean Cup |
| 1999-06-10 | CubavJamaicaCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 1999-06-07 | JamaicavGrenadaCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 1999-06-05 | JamaicavGuadeloupeCFU Caribbean Cup | 5–1 | CFU Caribbean Cup |
| 1999-06-03 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1998-07-31 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 1998-07-29 | JamaicavAntigua and BarbudaCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1998-07-26 | Jamaicav HaitiCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 1998-07-24 | JamaicavCuraçaoplayed as Netherlands AntillesCFU Caribbean Cup | 3–2 | CFU Caribbean Cup |
| 1998-07-22 | Jamaicav Cayman IslandsCFU Caribbean Cup | 4–0 | CFU Caribbean Cup |
| 1997-07-13 | JamaicavGrenadaCFU Caribbean Cup | 4–1 | CFU Caribbean Cup |
| 1997-07-10 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 1–1 p | CFU Caribbean Cup |
| 1997-07-08 | Antigua and BarbudavJamaicaCFU Caribbean Cup | 0–2 | CFU Caribbean Cup |
| 1997-07-04 | JamaicavGrenadaCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |
| 1996-05-28 |  SurinamevJamaicaCFU Caribbean Cup | 3–1 | CFU Caribbean Cup |
| 1996-05-26 | Jamaicav Saint Kitts and NevisCFU Caribbean Cup | 4–1 | CFU Caribbean Cup |
| 1996-05-24 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1995-07-23 | JamaicavTrinidad and TobagoCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1995-07-21 | JamaicavCubaCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 1995-07-19 | Jamaicav Saint LuciaCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 1993-05-30 | JamaicavMartiniqueCFU Caribbean Cup | 0–0 p | CFU Caribbean Cup |
| 1993-05-28 | JamaicavTrinidad and TobagoCFU Caribbean Cup | 3–0 | CFU Caribbean Cup |
| 1993-05-25 | Jamaicav Puerto RicoCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1993-05-23 | Jamaicav Sint MaartenCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 1993-05-21 | JamaicavSaint Kitts and NevisCFU Caribbean Cup | 4–1 | CFU Caribbean Cup |
| 1992-06-27 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 3–1 | CFU Caribbean Cup |
| 1992-06-24 | JamaicavMartiniqueCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1992-06-22 | CubavJamaicaCFU Caribbean Cup | 0–0 | CFU Caribbean Cup |
| 1992-06-20 | GuadeloupevJamaicaCFU Caribbean Cup | 0–1 | CFU Caribbean Cup |