| 2016-11-13 |  Jamaicav SurinameCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 2006-10-01 | Jamaicav HaitiCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 2006-09-27 | Jamaicav Saint LuciaCFU Caribbean Cup qualification | 4–0 | CFU Caribbean Cup qualification |
| 2005-01-15 |  French GuianavJamaicaCFU Caribbean Cup qualification | 0–0 | CFU Caribbean Cup qualification |
| 2005-01-08 | JamaicavFrench GuianaCFU Caribbean Cup qualification | 5–0 | CFU Caribbean Cup qualification |
| 2004-12-19 | JamaicavSaint LuciaCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 2004-12-12 | Saint LuciavJamaicaCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 2004-11-28 | JamaicavHaitiCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 2004-11-26 | Jamaicav United States Virgin IslandsCFU Caribbean Cup qualification | 11–1 | CFU Caribbean Cup qualification |
| 2004-11-24 | Jamaicav Saint MartinCFU Caribbean Cup qualification | 12–0 | CFU Caribbean Cup qualification |
| 1997-05-04 |  ArubavJamaicaCFU Caribbean Cup qualification | 0–6 | CFU Caribbean Cup qualification |
| 1997-02-23 | Jamaicav BermudaCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 1997-02-21 | JamaicavBermudaCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1996-04-28 |  BarbadosvJamaicaCFU Caribbean Cup qualification | 2–0 p | CFU Caribbean Cup qualification |
| 1996-04-24 | JamaicavBarbadosCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 1994-03-06 |  Cayman IslandsvJamaicaCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 1994-03-04 | Jamaicav British Virgin IslandsCFU Caribbean Cup qualification | 12–0 | CFU Caribbean Cup qualification |
| 1994-03-02 | Jamaicav Sint MaartenCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 1990-05-30 |  GuadeloupevJamaicaCFU Caribbean Cup qualification | 0–0 | CFU Caribbean Cup qualification |
| 1990-05-20 | JamaicavSaint MartinCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1990-04-29 | Jamaicav Saint Kitts and NevisCFU Caribbean Cup qualification | 3–0 | CFU Caribbean Cup qualification |
| 1989-06-18 | JamaicavSaint LuciaCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1989-06-04 |  DominicavJamaicaCFU Caribbean Cup qualification | 0–0 | CFU Caribbean Cup qualification |
| 1989-05-07 | JamaicavGuadeloupeCFU Caribbean Cup qualification | 1–3 | CFU Caribbean Cup qualification |
| 1989-04-23 |  Antigua and BarbudavJamaicaCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1979-11-02 | JamaicavHaitiCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 1979-10-28 | HaitivJamaicaCFU Caribbean Cup qualification | 3–0 | CFU Caribbean Cup qualification |
| 1979-06-17 | Saint Kitts and NevisvJamaicaCFU Caribbean Cup qualification | 1–2 | CFU Caribbean Cup qualification |
| 1979-06-03 | JamaicavSaint Kitts and NevisCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 1978-07-30 | JamaicavGuadeloupeCFU Caribbean Cup qualification | 1–2 | CFU Caribbean Cup qualification |
| 1978-07-02 | GuadeloupevJamaicaCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |