| 2016-03-26 |  Anguillav Puerto RicoCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 2014-09-05 |  Saint Vincent and the GrenadinesvAnguillaCFU Caribbean Cup qualification | 4–0 | CFU Caribbean Cup qualification |
| 2012-10-14 |  Trinidad and TobagovAnguillaCFU Caribbean Cup qualification | 10–0 | CFU Caribbean Cup qualification |
| 2012-10-12 |  French GuianavAnguillaCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 2010-10-06 | Anguillav Saint MartinCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 2010-10-04 |  Cayman IslandsvAnguillaCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 2010-10-02 | Puerto RicovAnguillaCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 2008-09-19 |  MartiniquevAnguillaCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 2006-09-24 |  BarbadosvAnguillaCFU Caribbean Cup qualification | 7–1 | CFU Caribbean Cup qualification |
| 2006-09-22 | Anguillav Saint Kitts and NevisCFU Caribbean Cup qualification | 1–6 | CFU Caribbean Cup qualification |
| 2006-09-20 |  Antigua and BarbudavAnguillaCFU Caribbean Cup qualification | 5–3 | CFU Caribbean Cup qualification |
| 2001-02-10 | Saint MartinvAnguillaCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 2001-02-08 | Anguillav MontserratCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 1998-04-19 |  GuyanavAnguillaCFU Caribbean Cup qualification | 14–0 | CFU Caribbean Cup qualification |
| 1998-04-15 |  GrenadavAnguillaCFU Caribbean Cup qualification | 14–1 | CFU Caribbean Cup qualification |
| 1997-04-06 |  DominicavAnguillaCFU Caribbean Cup qualification | 5–0 | CFU Caribbean Cup qualification |
| 1997-04-04 |  British Virgin IslandsvAnguillaCFU Caribbean Cup qualification | 4–2 | CFU Caribbean Cup qualification |
| 1997-04-02 |  Sint MaartenvAnguillaCFU Caribbean Cup qualification | 3–0 | CFU Caribbean Cup qualification |
| 1996-03-29 | Sint MaartenvAnguillaCFU Caribbean Cup qualification | 4–0 | CFU Caribbean Cup qualification |
| 1996-03-27 | Saint Kitts and NevisvAnguillaCFU Caribbean Cup qualification | 8–0 | CFU Caribbean Cup qualification |
| 1995-04-02 | AnguillavMontserratCFU Caribbean Cup qualification | 0–1 | CFU Caribbean Cup qualification |
| 1995-03-26 | MontserratvAnguillaCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 1994-03-06 | Saint Vincent and the GrenadinesvAnguillaCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 1994-03-04 |  GuadeloupevAnguillaCFU Caribbean Cup qualification | 9–0 | CFU Caribbean Cup qualification |
| 1993-04-06 | AnguillavSint MaartenCFU Caribbean Cup qualification | 0–1 | CFU Caribbean Cup qualification |
| 1993-04-04 | AnguillavAntigua and BarbudaCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 1992-05-09 |  CubavAnguillaCFU Caribbean Cup qualification | 5–0 | CFU Caribbean Cup qualification |
| 1992-05-02 | AnguillavCubaCFU Caribbean Cup qualification | 0–3 | CFU Caribbean Cup qualification |
| 1991-05-16 |  Saint LuciavAnguillaCFU Caribbean Cup qualification | 6–0 | CFU Caribbean Cup qualification |
| 1991-05-14 | AnguillavMontserratCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |