| 2026-06-06 |  Gibraltarv Cayman IslandsFriendly | 4–1 | Friendly |
| 2026-03-29 | Cayman Islandsv BahamasCONCACAF Series | 1–0 | CONCACAF Series |
| 2026-03-26 | Cayman Islandsv British Virgin IslandsCONCACAF Series | 1–1 | CONCACAF Series |
| 2025-11-15 | Cayman Islandsv AnguillaCONCACAF Series | 4–0 | CONCACAF Series |
| 2025-11-12 | Cayman IslandsvBritish Virgin IslandsCONCACAF Series | 1–2 | CONCACAF Series |
| 2025-06-07 | Cayman Islandsv HondurasFIFA World Cup qualification | 0–1 | FIFA World Cup qualification |
| 2025-06-04 |  BermudavCayman IslandsFIFA World Cup qualification | 5–0 | FIFA World Cup qualification |
| 2024-11-19 |  GuadeloupevCayman 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 IslandsvBritish 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 |
| 2024-06-11 |  CubavCayman IslandsFIFA World Cup qualification | 3–0 | FIFA World Cup qualification |
| 2024-06-08 | Cayman Islandsv Antigua and BarbudaFIFA World Cup qualification | 1–0 | FIFA World Cup qualification |
| 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 |
| 2021-06-08 | BermudavCayman IslandsFIFA World Cup qualification | 1–1 | FIFA World Cup qualification |
| 2021-06-02 | Cayman IslandsvArubaFIFA World Cup qualification | 1–3 | FIFA World Cup qualification |
| 2021-03-29 | Cayman Islandsv CanadaFIFA World Cup qualification | 0–11 | FIFA World Cup qualification |
| 2021-03-24 |  SurinamevCayman IslandsFIFA World Cup qualification | 3–0 | FIFA World Cup qualification |
| 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 |
| 2019-03-22 | Cayman Islandsv MontserratCONCACAF Nations League qualification | 1–2 | CONCACAF Nations League qualification |
| 2018-11-17 | Cayman Islandsv Saint LuciaCONCACAF Nations League qualification | 0–0 | CONCACAF Nations League qualification |
| 2018-10-12 |  Dominican RepublicvCayman IslandsCONCACAF Nations League qualification | 3–0 | CONCACAF Nations League qualification |
| 2018-09-09 |  JamaicavCayman IslandsCONCACAF Nations League qualification | 4–0 | CONCACAF Nations League qualification |
| 2015-05-13 | Dominican RepublicvCayman IslandsFriendly | 6–0 | Friendly |
| 2015-03-29 | Cayman Islandsv BelizeFIFA World Cup qualification | 1–1 | FIFA World Cup qualification |
| 2011-11-14 | Cayman IslandsvDominican RepublicFIFA World Cup qualification | 1–1 | FIFA World Cup qualification |
| 2011-11-11 | Dominican RepublicvCayman IslandsFIFA World Cup qualification | 4–0 | FIFA World Cup qualification |
| 2011-10-11 |  El SalvadorvCayman IslandsFIFA World Cup qualification | 4–0 | FIFA World Cup qualification |
| 2011-10-07 | Cayman IslandsvSurinameFIFA World Cup qualification | 0–1 | FIFA World Cup qualification |
| 2011-09-06 | Cayman IslandsvEl SalvadorFIFA World Cup qualification | 1–4 | FIFA World Cup qualification |
| 2011-09-02 | SurinamevCayman IslandsFIFA World Cup qualification | 1–0 | FIFA World Cup qualification |
| 2010-10-06 | Puerto RicovCayman IslandsCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 2010-10-04 | Cayman IslandsvAnguillaCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 2010-10-01 | Saint MartinvCayman IslandsCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 2009-06-28 | Cayman IslandsvJamaicaFriendly | 1–4 | Friendly |
| 2008-11-09 | Cayman IslandsvJamaicaFriendly | 0–2 | Friendly |