| 2008-10-15 |  Grenadav Cayman IslandsCFU Caribbean Cup qualification | 4–2 | CFU Caribbean Cup qualification |
| 2008-10-13 | Cayman Islandsv MartiniqueCFU Caribbean Cup qualification | 0–1 | CFU Caribbean Cup qualification |
| 2008-10-11 |  GuadeloupevCayman IslandsCFU Caribbean Cup qualification | 7–1 | CFU Caribbean Cup qualification |
| 2008-08-31 | Cayman Islandsv BermudaCFU Caribbean Cup qualification | 0–0 | CFU Caribbean Cup qualification |
| 2008-08-30 | Cayman Islandsv Antigua and BarbudaCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 2008-08-27 | Cayman Islandsv Saint MartinCFU Caribbean Cup qualification | 3–0 | CFU Caribbean Cup qualification |
| 2008-03-30 | Cayman IslandsvBermudaFIFA World Cup qualification | 1–3 | FIFA World Cup qualification |
| 2008-02-03 | BermudavCayman IslandsFIFA World Cup qualification | 1–1 | FIFA World Cup qualification |
| 2006-09-06 |  CubavCayman IslandsCFU Caribbean Cup qualification | 7–0 | CFU Caribbean Cup qualification |
| 2006-09-04 | Cayman Islandsv Turks and Caicos IslandsCFU Caribbean Cup qualification | 0–2 | CFU Caribbean Cup qualification |
| 2006-09-02 |  BahamasvCayman IslandsCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 2004-11-26 |  British Virgin IslandsvCayman IslandsCFU Caribbean Cup qualification | 0–1 | CFU Caribbean Cup qualification |
| 2004-11-24 | Cayman IslandsvBermudaCFU Caribbean Cup qualification | 1–2 | CFU Caribbean Cup qualification |
| 2004-03-27 | CubavCayman IslandsFIFA World Cup qualification | 3–0 | FIFA World Cup qualification |
| 2004-02-22 | Cayman IslandsvCubaFIFA World Cup qualification | 1–2 | FIFA World Cup qualification |
| 2002-12-01 | Cayman IslandsvMartiniqueGold Cup qualification | 0–3 | Gold Cup qualification |
| 2002-11-29 | Cayman Islandsv Dominican RepublicGold Cup qualification | 1–0 | Gold Cup qualification |
| 2002-11-27 | Cayman IslandsvCubaGold Cup qualification | 0–5 | Gold Cup qualification |
| 2002-11-17 | Cayman Islandsv NicaraguaFriendly | 0–1 | Friendly |
| 2001-04-08 | MartiniquevCayman IslandsCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 2001-04-04 | Cayman IslandsvBritish Virgin IslandsCFU Caribbean Cup qualification | 2–2 | CFU Caribbean Cup qualification |
| 2001-02-25 | Cayman Islandsv Trinidad and TobagoFriendly | 0–3 | Friendly |
| 2000-09-27 | Cayman IslandsvTurks and Caicos IslandsFriendly | 3–0 | Friendly |
| 2000-08-27 | Cayman Islandsv JamaicaFriendly | 0–6 | Friendly |
| 2000-03-19 | Cayman IslandsvCubaFIFA World Cup qualification | 0–0 | FIFA World Cup qualification |
| 2000-03-05 | CubavCayman IslandsFIFA World Cup qualification | 4–0 | FIFA World Cup qualification |
| 2000-02-09 | Cayman IslandsvJamaicaFriendly | 0–1 | Friendly |
| 2000-02-06 | Cayman IslandsvJamaicaFriendly | 0–0 | Friendly |
| 1999-10-24 | Cayman IslandsvJamaicaFriendly | 1–4 | Friendly |
| 1999-09-22 | Cayman IslandsvBahamasFriendly | 4–0 | Friendly |
| 1999-09-11 | BermudavCayman IslandsFriendly | 1–0 | Friendly |
| 1999-09-09 | BermudavCayman IslandsFriendly | 3–1 | Friendly |
| 1999-05-09 | Cayman IslandsvBahamasCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 1999-05-07 | BermudavCayman IslandsCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 1999-05-05 | CubavCayman IslandsCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 1998-07-26 |  Curaçaoplayed as Netherlands AntillesvCayman IslandsCFU Caribbean Cup | 0–2 | CFU Caribbean Cup |
| 1998-07-24 | Cayman Islandsv HaitiCFU Caribbean Cup | 0–1 | CFU Caribbean Cup |
| 1998-07-22 | JamaicavCayman IslandsCFU Caribbean Cup | 4–0 | CFU Caribbean Cup |
| 1998-05-10 | Cayman IslandsvBermudaCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 1998-05-06 | Cayman IslandsvCubaCFU Caribbean Cup qualification | 2–2 | CFU Caribbean Cup qualification |
| 1996-05-14 | Cayman IslandsvCubaFIFA World Cup qualification | 0–5 | FIFA World Cup qualification |
| 1996-05-12 | Cayman IslandsvCubaFIFA World Cup qualification | 0–1 | FIFA World Cup qualification |
| 1996-04-26 | Cayman IslandsvCubaCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 1995-10-24 | Cayman IslandsvTrinidad and TobagoFriendly | 0–7 | Friendly |
| 1995-10-22 | Cayman IslandsvJamaicaFriendly | 1–5 | Friendly |
| 1995-07-30 | Cayman IslandsvCubaCFU Caribbean Cup | 0–3 | CFU Caribbean Cup |
| 1995-07-28 | Cayman IslandsvTrinidad and TobagoCFU Caribbean Cup | 2–9 | CFU Caribbean Cup |
| 1995-07-23 | Cayman Islandsv French GuianaCFU Caribbean Cup | 1–0 | CFU Caribbean Cup |
| 1995-07-21 | Cayman IslandsvAntigua and BarbudaCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 1994-04-11 | MartiniquevCayman IslandsCFU Caribbean Cup | 1–1 | CFU Caribbean Cup |