| 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 |
| 2024-06-11 |  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 |
| 2021-06-08 | BermudavCayman IslandsFIFA World Cup qualification | 1–1 | FIFA World Cup qualification |
| 2021-06-02 | Cayman Islandsv ArubaFIFA 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 |
| 2015-03-29 | Cayman Islandsv BelizeFIFA World Cup qualification | 1–1 | FIFA World Cup qualification |
| 2011-11-14 | Cayman Islandsv Dominican 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 |
| 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 |
| 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 |
| 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 |
| 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 |