| 2008-12-07 |  Jamaicav Trinidad 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 Tobagov GrenadaCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 2008-11-19 | Trinidad and Tobagov CubaFIFA World Cup qualification | 3–0 | FIFA World Cup qualification |
| 2008-11-09 | Trinidad and Tobagov GuyanaCFU 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 Tobagov Antigua and BarbudaCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 2008-10-15 | Trinidad and Tobagov United StatesFIFA World Cup qualification | 2–1 | FIFA World Cup qualification |
| 2008-10-11 |  GuatemalavTrinidad and TobagoFIFA World Cup qualification | 0–0 | FIFA World Cup qualification |
| 2008-10-08 | Trinidad and Tobagov Dominican RepublicFriendly | 9–0 | Friendly |
| 2008-09-10 | United StatesvTrinidad and TobagoFIFA World Cup qualification | 3–0 | FIFA World Cup qualification |
| 2008-09-06 | Trinidad and TobagovGuatemalaFIFA World Cup qualification | 1–1 | FIFA World Cup qualification |
| 2008-09-03 | Trinidad and TobagovGuyanaFriendly | 3–0 | Friendly |
| 2008-08-20 | CubavTrinidad and TobagoFIFA World Cup qualification | 1–3 | FIFA World Cup qualification |
| 2008-08-14 |  El SalvadorvTrinidad and TobagoFriendly | 1–3 | Friendly |
| 2008-08-10 |  HaitivTrinidad and TobagoFriendly | 1–0 | Friendly |
| 2008-07-30 | Trinidad and TobagovHaitiFriendly | 2–0 | Friendly |
| 2008-07-17 | Trinidad and Tobagov Curaçaoplayed as Netherlands AntillesFriendly | 2–0 | Friendly |
| 2008-07-08 | Trinidad and TobagovGuyanaFriendly | 2–0 | Friendly |
| 2008-06-22 |  BermudavTrinidad and TobagoFIFA World Cup qualification | 0–2 | FIFA World Cup qualification |
| 2008-06-15 | Trinidad and TobagovBermudaFIFA World Cup qualification | 1–2 | FIFA World Cup qualification |
| 2008-06-07 | Trinidad and TobagovJamaicaFriendly | 1–1 | Friendly |
| 2008-06-01 | Trinidad and Tobagov EnglandFriendly | 0–3 | Friendly |
| 2008-05-11 | Trinidad and TobagovBarbadosFriendly | 3–0 | Friendly |
| 2008-04-27 | Trinidad and TobagovGrenadaFriendly | 2–0 | Friendly |
| 2008-03-26 | JamaicavTrinidad and TobagoFriendly | 2–2 | Friendly |
| 2008-03-19 | Trinidad and TobagovEl SalvadorFriendly | 1–0 | Friendly |
| 2008-02-06 | Trinidad and Tobagov GuadeloupeFriendly | 0–0 | Friendly |
| 2008-01-29 | Trinidad and TobagovGuyanaFriendly | 2–1 | Friendly |
| 2008-01-26 |  Puerto RicovTrinidad and TobagoFriendly | 2–2 | Friendly |