| 2017-01-08 |  Trinidad and Tobagov HaitiCFU Caribbean Cup qualification | 3–4 | CFU Caribbean Cup qualification |
| 2017-01-04 | Trinidad and Tobagov SurinameCFU Caribbean Cup qualification | 1–2 | CFU Caribbean Cup qualification |
| 2016-10-05 | Trinidad and Tobagov Dominican RepublicCFU Caribbean Cup qualification | 4–0 | CFU Caribbean Cup qualification |
| 2014-10-12 | Trinidad and Tobagov Antigua and BarbudaCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 2014-10-10 | Trinidad and Tobagov Saint LuciaCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 2014-10-08 | Trinidad and TobagovDominican RepublicCFU Caribbean Cup qualification | 6–1 | CFU Caribbean Cup qualification |
| 2012-11-16 | Trinidad and TobagovSurinameCFU Caribbean Cup qualification | 3–0 | CFU Caribbean Cup qualification |
| 2012-10-14 | Trinidad and Tobagov AnguillaCFU Caribbean Cup qualification | 10–0 | CFU Caribbean Cup qualification |
| 2012-10-10 |  French GuianavTrinidad and TobagoCFU Caribbean Cup qualification | 1–4 | CFU Caribbean Cup qualification |
| 2010-11-06 | Trinidad and TobagovHaitiCFU Caribbean Cup qualification | 4–0 | CFU Caribbean Cup qualification |
| 2010-11-04 | Trinidad and Tobagov GuyanaCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 2008-11-09 | Trinidad and TobagovGuyanaCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 2008-11-07 | Trinidad and Tobagov Saint Kitts and NevisCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 2008-11-05 | Trinidad and TobagovAntigua and BarbudaCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 2004-12-19 | Trinidad and Tobagov British Virgin IslandsCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 2004-12-12 | British Virgin IslandsvTrinidad and TobagoCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 2004-11-28 | Trinidad and TobagovSurinameCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 2004-11-26 | Trinidad and Tobagov GrenadaCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 2004-11-24 | Trinidad and Tobagov Puerto RicoCFU Caribbean Cup qualification | 5–0 | CFU Caribbean Cup qualification |
| 1989-06-06 | GrenadavTrinidad and TobagoCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1989-05-21 | Saint Kitts and NevisvTrinidad and TobagoCFU Caribbean Cup qualification | 0–2 | CFU Caribbean Cup qualification |
| 1989-05-10 | French GuianavTrinidad and TobagoCFU Caribbean Cup qualification | 1–3 | CFU Caribbean Cup qualification |
| 1989-04-23 | Trinidad and Tobagov ArubaCFU Caribbean Cup qualification | 11–0 | CFU Caribbean Cup qualification |
| 1987-12-06 | Trinidad and Tobagov BarbadosCFU Caribbean Cup qualification | 5–1 | CFU Caribbean Cup qualification |
| 1987-11-29 | BarbadosvTrinidad and TobagoCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 1985-05-05 | Trinidad and TobagovSurinameCFU Caribbean Cup qualification | 0–1 | CFU Caribbean Cup qualification |
| 1985-04-03 |  GuadeloupevTrinidad and TobagoCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1985-03-03 | GrenadavTrinidad and TobagoCFU Caribbean Cup qualification | 1–5 | CFU Caribbean Cup qualification |
| 1985-02-24 |  Saint Vincent and the GrenadinesvTrinidad and TobagoCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1981-08-14 | Trinidad and TobagovSurinameCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 1981-08-02 | SurinamevTrinidad and TobagoCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1981-07-17 | Trinidad and TobagovBarbadosCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1981-07-05 | BarbadosvTrinidad and TobagoCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1979-08-04 | Trinidad and TobagovGrenadaCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 1979-07-22 | GrenadavTrinidad and TobagoCFU Caribbean Cup qualification | 0–1 | CFU Caribbean Cup qualification |
| 1978-09-02 | French GuianavTrinidad and TobagoCFU Caribbean Cup qualification | 1–4 | CFU Caribbean Cup qualification |
| 1978-08-20 | Trinidad and TobagovFrench GuianaCFU Caribbean Cup qualification | 2–4 | CFU Caribbean Cup qualification |