| 2025-06-24 |  Panamav JamaicaGold Cup | 4–1 | Gold Cup |
| 2025-06-20 | Jamaicav GuadeloupeGold Cup | 2–1 | Gold Cup |
| 2025-06-16 | Jamaicav GuatemalaGold Cup | 0–1 | Gold Cup |
| 2023-07-12 | Jamaicav MexicoGold Cup | 0–3 | Gold Cup |
| 2023-07-09 | GuatemalavJamaicaGold Cup | 0–1 | Gold Cup |
| 2023-07-02 | Jamaicav Saint Kitts and NevisGold Cup | 5–0 | Gold Cup |
| 2023-06-28 | Jamaicav Trinidad and TobagoGold Cup | 4–1 | Gold Cup |
| 2023-06-24 |  United StatesvJamaicaGold Cup | 1–1 | Gold Cup |
| 2021-07-25 | United StatesvJamaicaGold Cup | 1–0 | Gold Cup |
| 2021-07-20 |  Costa RicavJamaicaGold Cup | 1–0 | Gold Cup |
| 2021-07-16 | GuadeloupevJamaicaGold Cup | 1–2 | Gold Cup |
| 2021-07-12 | Jamaicav SurinameGold Cup | 2–0 | Gold Cup |
| 2019-07-03 | United StatesvJamaicaGold Cup | 3–1 | Gold Cup |
| 2019-06-30 | JamaicavPanamaGold Cup | 1–0 | Gold Cup |
| 2019-06-25 | Jamaicav CuraçaoGold Cup | 1–1 | Gold Cup |
| 2019-06-21 |  El SalvadorvJamaicaGold Cup | 0–0 | Gold Cup |
| 2019-06-17 | Jamaicav HondurasGold Cup | 3–2 | Gold Cup |
| 2017-07-26 | United StatesvJamaicaGold Cup | 2–1 | Gold Cup |
| 2017-07-23 | MexicovJamaicaGold Cup | 0–1 | Gold Cup |
| 2017-07-20 | Jamaicav CanadaGold Cup | 2–1 | Gold Cup |
| 2017-07-16 | JamaicavEl SalvadorGold Cup | 1–1 | Gold Cup |
| 2017-07-13 | MexicovJamaicaGold Cup | 0–0 | Gold Cup |
| 2017-07-09 | CuraçaovJamaicaGold Cup | 0–2 | Gold Cup |
| 2015-07-26 | JamaicavMexicoGold Cup | 1–3 | Gold Cup |
| 2015-07-22 | United StatesvJamaicaGold Cup | 1–2 | Gold Cup |
| 2015-07-18 |  HaitivJamaicaGold Cup | 0–1 | Gold Cup |
| 2015-07-14 | JamaicavEl SalvadorGold Cup | 1–0 | Gold Cup |
| 2015-07-11 | JamaicavCanadaGold Cup | 1–0 | Gold Cup |
| 2015-07-08 | Costa RicavJamaicaGold Cup | 2–2 | Gold Cup |
| 2011-06-19 | United StatesvJamaicaGold Cup | 2–0 | Gold Cup |
| 2011-06-13 | HondurasvJamaicaGold Cup | 0–1 | Gold Cup |
| 2011-06-10 | JamaicavGuatemalaGold Cup | 2–0 | Gold Cup |
| 2011-06-06 | Jamaicav GrenadaGold Cup | 4–0 | Gold Cup |
| 2009-07-10 | El SalvadorvJamaicaGold Cup | 0–1 | Gold Cup |
| 2009-07-07 | JamaicavCosta RicaGold Cup | 0–1 | Gold Cup |
| 2009-07-03 | CanadavJamaicaGold Cup | 1–0 | Gold Cup |
| 2005-07-16 | United StatesvJamaicaGold Cup | 3–1 | Gold Cup |
| 2005-07-13 | MexicovJamaicaGold Cup | 1–0 | Gold Cup |
| 2005-07-10 | Jamaicav South AfricaGold Cup | 3–3 | Gold Cup |
| 2005-07-08 | GuatemalavJamaicaGold Cup | 3–4 | Gold Cup |
| 2003-07-20 | MexicovJamaicaGold Cup | 5–0 | Gold Cup |
| 2003-07-15 | GuatemalavJamaicaGold Cup | 0–2 | Gold Cup |
| 2003-07-13 | Jamaicav ColombiaGold Cup | 0–1 | Gold Cup |
| 2000-02-14 | JamaicavHondurasGold Cup | 0–2 | Gold Cup |
| 2000-02-12 | ColombiavJamaicaGold Cup | 1–0 | Gold Cup |
| 1998-02-15 |  BrazilvJamaicaGold Cup | 1–0 | Gold Cup |
| 1998-02-12 | JamaicavMexicoGold Cup | 0–1 | Gold Cup |
| 1998-02-09 | JamaicavEl SalvadorGold Cup | 2–0 | Gold Cup |
| 1998-02-08 | GuatemalavJamaicaGold Cup | 2–3 | Gold Cup |
| 1998-02-03 | BrazilvJamaicaGold Cup | 0–0 | Gold Cup |