| 2008-12-14 |  Jamaicav GrenadaCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 2008-12-11 | Jamaicav GuadeloupeCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 2008-12-07 | Jamaicav Trinidad and TobagoCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |
| 2008-12-05 | JamaicavGrenadaCFU Caribbean Cup | 4–0 | CFU Caribbean Cup |
| 2008-12-03 | Jamaicav BarbadosCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 2008-11-19 | Jamaicav CanadaFIFA World Cup qualification | 3–0 | FIFA World Cup qualification |
| 2008-11-09 |  Cayman IslandsvJamaicaFriendly | 0–2 | Friendly |
| 2008-10-15 | Jamaicav HondurasFIFA World Cup qualification | 1–0 | FIFA World Cup qualification |
| 2008-10-11 | Jamaicav MexicoFIFA World Cup qualification | 1–0 | FIFA World Cup qualification |
| 2008-09-10 | HondurasvJamaicaFIFA World Cup qualification | 2–0 | FIFA World Cup qualification |
| 2008-09-06 | MexicovJamaicaFIFA World Cup qualification | 3–0 | FIFA World Cup qualification |
| 2008-08-20 | CanadavJamaicaFIFA World Cup qualification | 1–1 | FIFA World Cup qualification |
| 2008-07-26 |  El SalvadorvJamaicaFriendly | 0–0 | Friendly |
| 2008-06-18 | Jamaicav BahamasFIFA World Cup qualification | 6–0 | FIFA World Cup qualification |
| 2008-06-15 | JamaicavBahamasFIFA World Cup qualification | 7–0 | FIFA World Cup qualification |
| 2008-06-10 | GrenadavJamaicaFriendly | 2–1 | Friendly |
| 2008-06-07 | Trinidad and TobagovJamaicaFriendly | 1–1 | Friendly |
| 2008-03-26 | JamaicavTrinidad and TobagoFriendly | 2–2 | Friendly |
| 2008-02-06 | Jamaicav Costa RicaFriendly | 1–1 | Friendly |