| 2016-06-19 |  French Guianav BermudaCFU Caribbean Cup qualification | 3–0 | CFU Caribbean Cup qualification |
| 2016-03-26 | BermudavFrench GuianaCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 2016-03-22 |  CubavBermudaCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 2012-09-11 |  Saint MartinvBermudaCFU Caribbean Cup qualification | 0–8 | CFU Caribbean Cup qualification |
| 2012-09-09 |  HaitivBermudaCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 2012-09-07 | Bermudav Puerto RicoCFU Caribbean Cup qualification | 1–2 | CFU Caribbean Cup qualification |
| 2008-08-31 |  Cayman IslandsvBermudaCFU Caribbean Cup qualification | 0–0 | CFU Caribbean Cup qualification |
| 2008-08-30 | Saint MartinvBermudaCFU Caribbean Cup qualification | 0–7 | CFU Caribbean Cup qualification |
| 2008-08-27 | Bermudav Antigua and BarbudaCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 2007-01-09 | BermudavHaitiCFU Caribbean Cup qualification | 0–3 | CFU Caribbean Cup qualification |
| 2007-01-07 | HaitivBermudaCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 2006-11-23 |  BarbadosvBermudaCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 2006-11-21 |  BahamasvBermudaCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 2006-09-29 | Bermudav Dominican RepublicCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 2006-09-27 |  United States Virgin IslandsvBermudaCFU Caribbean Cup qualification | 0–6 | CFU Caribbean Cup qualification |
| 2004-11-28 | Bermudav British Virgin IslandsCFU Caribbean Cup qualification | 0–2 | CFU Caribbean Cup qualification |
| 2004-11-24 | Cayman IslandsvBermudaCFU Caribbean Cup qualification | 1–2 | CFU Caribbean Cup qualification |
| 1999-05-09 | BermudavCubaCFU Caribbean Cup qualification | 1–2 | CFU Caribbean Cup qualification |
| 1999-05-07 | BermudavCayman IslandsCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 1999-05-05 | BermudavBahamasCFU Caribbean Cup qualification | 6–0 | CFU Caribbean Cup qualification |
| 1998-05-10 | Cayman IslandsvBermudaCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 1998-05-08 | CubavBermudaCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 1997-02-23 |  JamaicavBermudaCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 1997-02-21 | JamaicavBermudaCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1990-05-26 | BermudavBarbadosCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1990-05-13 |  Saint LuciavBermudaCFU Caribbean Cup qualification | 0–2 | CFU Caribbean Cup qualification |
| 1990-04-14 | BermudavAntigua and BarbudaCFU Caribbean Cup qualification | 2–2 | CFU Caribbean Cup qualification |