| 1999-09-02 |  Canadav JamaicaFriendly | 1–0 | Friendly |
| 1999-08-07 |  GhanavJamaicaFriendly | 2–1 | Friendly |
| 1999-07-15 | Jamaicav Saudi ArabiaFriendly | 0–4 | Friendly |
| 1999-07-13 | JamaicavSaudi ArabiaFriendly | 2–1 | Friendly |
| 1999-06-10 |  CubavJamaicaCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 1999-06-07 | Jamaicav GrenadaCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 1999-06-05 | Jamaicav GuadeloupeCFU Caribbean Cup | 5–1 | CFU Caribbean Cup |
| 1999-06-03 |  Trinidad and TobagovJamaicaCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1999-05-27 |  SwedenvJamaicaFriendly | 2–1 | Friendly |
| 1999-05-20 |  NorwayvJamaicaFriendly | 6–0 | Friendly |
| 1999-05-09 | Jamaicav South AfricaFriendly | 1–1 | Friendly |
| 1999-03-31 | Jamaicav ParaguayFriendly | 3–0 | Friendly |
| 1999-03-28 | Trinidad and TobagovJamaicaFriendly | 2–0 | Friendly |
| 1999-03-07 |  GuatemalavJamaicaFriendly | 2–4 | Friendly |
| 1999-03-05 | JamaicavParaguayFriendly | 1–3 | Friendly |
| 1999-03-03 |  BoliviavJamaicaFriendly | 0–0 | Friendly |
| 1999-02-24 |  Costa RicavJamaicaFriendly | 9–0 | Friendly |
| 1999-02-10 | JamaicavCosta RicaFriendly | 1–1 | Friendly |
| 1998-07-31 | Trinidad and TobagovJamaicaCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 1998-07-29 | Jamaicav Antigua and BarbudaCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1998-07-26 | Jamaicav HaitiCFU Caribbean Cup | 2–1 | CFU Caribbean Cup |
| 1998-07-24 | Jamaicav Curaçaoplayed as Netherlands AntillesCFU Caribbean Cup | 3–2 | CFU Caribbean Cup |
| 1998-07-22 | Jamaicav Cayman IslandsCFU Caribbean Cup | 4–0 | CFU Caribbean Cup |
| 1998-06-26 |  JapanvJamaicaFIFA World Cup | 1–2 | FIFA World Cup |
| 1998-06-21 |  ArgentinavJamaicaFIFA World Cup | 5–0 | FIFA World Cup |
| 1998-06-14 | Jamaicav CroatiaFIFA World Cup | 1–3 | FIFA World Cup |
| 1998-05-19 |  South KoreavJamaicaFriendly | 0–0 | Friendly |
| 1998-05-16 | South KoreavJamaicaFriendly | 2–1 | Friendly |
| 1998-05-04 | JamaicavSaudi ArabiaFriendly | 0–0 | Friendly |
| 1998-04-22 |  IranvJamaicaFriendly | 1–0 | Friendly |
| 1998-04-20 | Jamaicav North Macedoniaplayed as MacedoniaFriendly | 1–2 | Friendly |
| 1998-03-25 |  WalesvJamaicaFriendly | 0–0 | Friendly |
| 1998-02-22 | Jamaicav NigeriaFriendly | 2–2 | Friendly |
| 1998-02-15 |  BrazilvJamaicaGold Cup | 1–0 | Gold Cup |
| 1998-02-12 | Jamaicav MexicoGold Cup | 0–1 | Gold Cup |
| 1998-02-09 | Jamaicav El SalvadorGold Cup | 2–0 | Gold Cup |
| 1998-02-08 | GuatemalavJamaicaGold Cup | 2–3 | Gold Cup |
| 1998-02-03 | BrazilvJamaicaGold Cup | 0–0 | Gold Cup |
| 1998-01-29 | JamaicavSwedenFriendly | 0–0 | Friendly |
| 1998-01-07 | Trinidad and TobagovJamaicaFriendly | 0–0 | Friendly |
| 1997-11-16 | JamaicavMexicoFIFA World Cup qualification | 0–0 | FIFA World Cup qualification |
| 1997-11-09 | El SalvadorvJamaicaFIFA World Cup qualification | 2–2 | FIFA World Cup qualification |
| 1997-10-29 |  Saint Kitts and NevisvJamaicaFriendly | 1–1 | Friendly |
| 1997-10-26 | Antigua and BarbudavJamaicaFriendly | 0–3 | Friendly |
| 1997-10-24 |  Saint LuciavJamaicaFriendly | 1–3 | Friendly |
| 1997-10-18 | HaitivJamaicaFriendly | 0–1 | Friendly |
| 1997-10-03 |  United StatesvJamaicaFIFA World Cup qualification | 1–1 | FIFA World Cup qualification |
| 1997-09-14 | JamaicavCosta RicaFIFA World Cup qualification | 1–0 | FIFA World Cup qualification |
| 1997-09-07 | JamaicavCanadaFIFA World Cup qualification | 1–0 | FIFA World Cup qualification |
| 1997-08-31 | JamaicavTrinidad and TobagoFriendly | 6–1 | Friendly |