| 2024-11-19 |  Guadeloupev Cayman IslandsCONCACAF Nations League | 1–0 | CONCACAF Nations League |
| 2024-11-15 | Cayman IslandsvGuadeloupeCONCACAF Nations League | 0–6 | CONCACAF Nations League |
| 2024-10-15 |  Saint Kitts and NevisvCayman IslandsCONCACAF Nations League | 1–1 | CONCACAF Nations League |
| 2024-10-12 | Cayman Islandsv British Virgin IslandsCONCACAF Nations League | 1–0 | CONCACAF Nations League |
| 2024-09-07 | Cayman IslandsvSaint Kitts and NevisCONCACAF Nations League | 1–4 | CONCACAF Nations League |
| 2024-09-04 | Cayman IslandsvBritish Virgin IslandsCONCACAF Nations League | 1–0 | CONCACAF Nations League |
| 2023-11-20 |  ArubavCayman IslandsCONCACAF Nations League | 5–1 | CONCACAF Nations League |
| 2023-10-17 | Cayman Islandsv United States Virgin IslandsCONCACAF Nations League | 2–1 | CONCACAF Nations League |
| 2023-09-11 | Cayman IslandsvArubaCONCACAF Nations League | 1–2 | CONCACAF Nations League |
| 2023-09-07 | United States Virgin IslandsvCayman IslandsCONCACAF Nations League | 2–2 | CONCACAF Nations League |
| 2023-03-26 |  Puerto RicovCayman IslandsCONCACAF Nations League | 5–1 | CONCACAF Nations League |
| 2022-06-09 | Cayman IslandsvPuerto RicoCONCACAF Nations League | 0–3 | CONCACAF Nations League |
| 2022-06-06 | Cayman IslandsvBritish Virgin IslandsCONCACAF Nations League | 1–1 | CONCACAF Nations League |
| 2022-06-03 | British Virgin IslandsvCayman IslandsCONCACAF Nations League | 1–1 | CONCACAF Nations League |
| 2019-11-19 |  BarbadosvCayman IslandsCONCACAF Nations League | 3–0 | CONCACAF Nations League |
| 2019-11-16 | Cayman IslandsvUnited States Virgin IslandsCONCACAF Nations League | 1–0 | CONCACAF Nations League |
| 2019-10-15 | Cayman Islandsv Saint MartinCONCACAF Nations League | 1–0 | CONCACAF Nations League |
| 2019-10-12 | Saint MartinvCayman IslandsCONCACAF Nations League | 3–0 | CONCACAF Nations League |
| 2019-09-08 | Cayman IslandsvBarbadosCONCACAF Nations League | 3–2 | CONCACAF Nations League |
| 2019-09-05 | United States Virgin IslandsvCayman IslandsCONCACAF Nations League | 0–2 | CONCACAF Nations League |