| 1994-04-09 |  Surinamev Cayman IslandsCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 1994-04-07 | Cayman Islandsv HaitiCFU Caribbean Cup | 2–3 | CFU Caribbean Cup |
| 1994-03-06 | Cayman Islandsv JamaicaCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 1994-03-04 | Cayman Islandsv Sint MaartenCFU Caribbean Cup qualification | 5–0 | CFU Caribbean Cup qualification |
| 1994-03-02 | Cayman Islandsv British Virgin IslandsCFU Caribbean Cup qualification | 5–0 | CFU Caribbean Cup qualification |
| 1993-11-14 |  United StatesvCayman IslandsFriendly | 8–1 | Friendly |
| 1993-03-14 |  Puerto RicovCayman IslandsCFU Caribbean Cup qualification | 4–0 | CFU Caribbean Cup qualification |
| 1993-03-12 | Cayman Islandsv BarbadosCFU Caribbean Cup qualification | 1–6 | CFU Caribbean Cup qualification |
| 1993-03-11 |  GuyanavCayman IslandsCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 1992-04-03 | Sint MaartenvCayman IslandsCFU Caribbean Cup qualification | 4–2 | CFU Caribbean Cup qualification |
| 1992-04-01 | Cayman Islandsv MartiniqueCFU Caribbean Cup qualification | 0–7 | CFU Caribbean Cup qualification |
| 1991-05-28 | Cayman IslandsvGuyanaCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 1991-05-26 | JamaicavCayman IslandsCFU Caribbean Cup | 3–2 | CFU Caribbean Cup |
| 1991-05-12 |  Saint Kitts and NevisvCayman IslandsCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1991-05-10 | Cayman IslandsvBritish Virgin IslandsCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 1990-05-06 | Cayman IslandsvJamaicaFriendly | 1–2 | Friendly |
| 1990-03-24 | Sint MaartenvCayman IslandsCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1987-02-07 | Cayman IslandsvJamaicaFriendly | 1–3 | Friendly |
| 1985-03-03 |  DominicavCayman IslandsCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |