| 1994-04-17 |  Trinidad and Tobagov MartiniqueCFU Caribbean Cup | 7–2 | CFU Caribbean Cup |
| 1994-04-14 | Trinidad and Tobagov SurinameCFU Caribbean Cup | 3–2 | CFU Caribbean Cup |
| 1993-05-30 | Trinidad and Tobagov Saint Kitts and NevisCFU Caribbean Cup | 3–2 | CFU Caribbean Cup |
| 1993-05-28 |  JamaicavTrinidad and TobagoCFU Caribbean Cup | 3–0 | CFU Caribbean Cup |
| 1993-05-25 | MartiniquevTrinidad and TobagoCFU Caribbean Cup | 3–2 | CFU Caribbean Cup |
| 1993-05-23 | Trinidad and Tobagov Saint LuciaCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |
| 1992-06-27 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 3–1 | CFU Caribbean Cup |
| 1992-06-24 | Trinidad and Tobagov CubaCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1991-06-02 | JamaicavTrinidad and TobagoCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 1991-05-30 |  GuyanavTrinidad and TobagoCFU Caribbean Cup | 1–3 | CFU Caribbean Cup |
| 1991-05-27 | Saint LuciavTrinidad and TobagoCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 1991-05-25 | MartiniquevTrinidad and TobagoCFU Caribbean Cup | 0–1 | CFU Caribbean Cup |
| 1991-05-23 |  Dominican RepublicvTrinidad and TobagoCFU Caribbean Cup | 0–7 | CFU Caribbean Cup |
| 1990-07-27 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 0–0 | CFU Caribbean Cup |
| 1989-07-09 |  GrenadavTrinidad and TobagoCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 1989-07-07 |  GuadeloupevTrinidad and TobagoCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 1989-07-05 |  BarbadosvTrinidad and TobagoCFU Caribbean Cup | 0–3 | CFU Caribbean Cup |
| 1988-07-09 | MartiniquevTrinidad and TobagoCFU Caribbean Cup | 0–3 | CFU Caribbean Cup |
| 1988-07-07 |  Antigua and BarbudavTrinidad and TobagoCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |
| 1988-07-05 | GuadeloupevTrinidad and TobagoCFU Caribbean Cup | 0–3 | CFU Caribbean Cup |
| 1983-07-27 | Antigua and BarbudavTrinidad and TobagoCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 1983-07-25 | MartiniquevTrinidad and TobagoCFU Caribbean Cup | 3–1 | CFU Caribbean Cup |
| 1983-07-23 |  French GuianavTrinidad and TobagoCFU Caribbean Cup | 0–1 | CFU Caribbean Cup |
| 1981-10-21 | GuadeloupevTrinidad and TobagoCFU Caribbean Cup | 0–2 | CFU Caribbean Cup |
| 1981-10-19 |  Saint Vincent and the GrenadinesvTrinidad and TobagoCFU Caribbean Cup | 0–2 | CFU Caribbean Cup |
| 1979-11-15 | SurinamevTrinidad and TobagoCFU Caribbean Cup | 3–0 | CFU Caribbean Cup |
| 1979-11-11 |  HaitivTrinidad and TobagoCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1978-10-29 | Trinidad and TobagovHaitiCFU Caribbean Cup | 2–2 | CFU Caribbean Cup |
| 1978-10-25 | Trinidad and TobagovSurinameCFU Caribbean Cup | 0–1 | CFU Caribbean Cup |
| 1978-10-23 | Trinidad and TobagovAntigua and BarbudaCFU Caribbean Cup | 3–1 | CFU Caribbean Cup |