| 2014-11-18 |  Jamaicav Trinidad and TobagoCFU Caribbean Cup | 0–0 | CFU Caribbean Cup |
| 2014-11-13 | Trinidad and Tobagov French GuianaCFU Caribbean Cup | 4–2 | CFU Caribbean Cup |
| 2014-11-11 |  CuraçaovTrinidad and TobagoCFU Caribbean Cup | 2–3 | CFU Caribbean Cup |
| 2012-12-16 |  CubavTrinidad and TobagoCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 2012-12-14 |  MartiniquevTrinidad and TobagoCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |
| 2012-12-11 | Trinidad and Tobagov Dominican RepublicCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 2012-12-09 |  Antigua and BarbudavTrinidad and TobagoCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 2012-12-07 |  HaitivTrinidad and TobagoCFU Caribbean Cup | 0–0 | CFU Caribbean Cup |
| 2010-11-30 | MartiniquevTrinidad and TobagoCFU Caribbean Cup | 0–1 | CFU Caribbean Cup |
| 2010-11-28 |  GrenadavTrinidad and TobagoCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 2010-11-26 | Trinidad and TobagovCubaCFU Caribbean Cup | 0–2 | CFU Caribbean Cup |
| 2008-12-07 | JamaicavTrinidad and TobagoCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |
| 2008-12-05 |  BarbadosvTrinidad and TobagoCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 2008-12-03 | Trinidad and TobagovGrenadaCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 2007-01-23 | Trinidad and TobagovHaitiCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 2007-01-20 | Trinidad and TobagovCubaCFU Caribbean Cup | 3–1 | CFU Caribbean Cup |
| 2007-01-17 | Trinidad and TobagovHaitiCFU Caribbean Cup | 3–1 | CFU Caribbean Cup |
| 2007-01-15 | Trinidad and TobagovMartiniqueCFU Caribbean Cup | 5–1 | CFU Caribbean Cup |
| 2007-01-12 | Trinidad and TobagovBarbadosCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |
| 2005-02-24 | BarbadosvTrinidad and TobagoCFU Caribbean Cup | 2–3 | CFU Caribbean Cup |
| 2005-02-22 | Trinidad and TobagovCubaCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 2005-02-20 | JamaicavTrinidad and TobagoCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 2001-05-25 | Trinidad and TobagovHaitiCFU Caribbean Cup | 3–0 | CFU Caribbean Cup |
| 2001-05-22 | Trinidad and TobagovCubaCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 2001-05-19 | Trinidad and TobagovMartiniqueCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 2001-05-17 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 2001-05-15 | Trinidad and TobagovBarbadosCFU Caribbean Cup | 5–0 | CFU Caribbean Cup |
| 1999-06-13 | Trinidad and TobagovCubaCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 1999-06-11 | Trinidad and TobagovHaitiCFU Caribbean Cup | 6–1 | CFU Caribbean Cup |
| 1999-06-07 | Trinidad and Tobagov GuadeloupeCFU Caribbean Cup | 3–2 | CFU Caribbean Cup |
| 1999-06-05 | Trinidad and TobagovGrenadaCFU Caribbean Cup | 7–0 | 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 | Trinidad and TobagovHaitiCFU Caribbean Cup | 4–1 | CFU Caribbean Cup |
| 1998-07-26 | Trinidad and Tobagov DominicaCFU Caribbean Cup | 8–0 | CFU Caribbean Cup |
| 1998-07-24 | Trinidad and TobagovMartiniqueCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 1998-07-22 | Trinidad and TobagovAntigua and BarbudaCFU Caribbean Cup | 3–2 | CFU Caribbean Cup |
| 1997-07-13 | Trinidad and Tobagov Saint Kitts and NevisCFU Caribbean Cup | 4–0 | CFU Caribbean Cup |
| 1997-07-10 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 1–1 p | CFU Caribbean Cup |
| 1997-07-08 | Saint Kitts and NevisvTrinidad and TobagoCFU Caribbean Cup | 0–3 | CFU Caribbean Cup |
| 1997-07-04 | MartiniquevTrinidad and TobagoCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 1996-06-07 | Trinidad and TobagovCubaCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 1996-06-02 | Trinidad and TobagovMartiniqueCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 1996-05-28 | Trinidad and TobagovSaint Kitts and NevisCFU Caribbean Cup | 5–1 | CFU Caribbean Cup |
| 1996-05-26 | Trinidad and Tobagov SurinameCFU Caribbean Cup | 3–0 | CFU Caribbean Cup |
| 1996-05-24 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1995-07-28 |  Cayman IslandsvTrinidad and TobagoCFU Caribbean Cup | 2–9 | CFU Caribbean Cup |
| 1995-07-23 | JamaicavTrinidad and TobagoCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1995-07-21 |  Saint LuciavTrinidad and TobagoCFU Caribbean Cup | 0–5 | CFU Caribbean Cup |
| 1995-07-19 | Trinidad and TobagovCubaCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |