| 2016-03-29 |  Dominican Republicv BarbadosCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 2016-03-23 | Barbadosv CuraçaoCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 2014-10-12 | Barbadosv French GuianaCFU Caribbean Cup qualification | 0–2 | CFU Caribbean Cup qualification |
| 2014-10-08 |  Saint Kitts and NevisvBarbadosCFU Caribbean Cup qualification | 2–3 | CFU Caribbean Cup qualification |
| 2014-09-07 |  BonairevBarbadosCFU Caribbean Cup qualification | 1–4 | CFU Caribbean Cup qualification |
| 2012-09-27 | Barbadosv ArubaCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 2012-09-25 | BarbadosvDominican RepublicCFU Caribbean Cup qualification | 0–1 | CFU Caribbean Cup qualification |
| 2012-09-23 | Barbadosv DominicaCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 2010-10-08 |  MontserratvBarbadosCFU Caribbean Cup qualification | 0–5 | CFU Caribbean Cup qualification |
| 2010-10-06 | BarbadosvSaint Kitts and NevisCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 2008-10-27 | Curaçaoplayed as Netherlands AntillesvBarbadosCFU Caribbean Cup qualification | 1–2 | CFU Caribbean Cup qualification |
| 2008-10-25 |  CubavBarbadosCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 2008-10-23 | Barbadosv SurinameCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 2008-09-28 | Saint Kitts and NevisvBarbadosCFU Caribbean Cup qualification | 1–3 | CFU Caribbean Cup qualification |
| 2008-09-26 |  British Virgin IslandsvBarbadosCFU Caribbean Cup qualification | 1–2 | CFU Caribbean Cup qualification |
| 2006-11-23 | Barbadosv BermudaCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 2006-11-19 | Barbadosv BahamasCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 2006-09-24 | Barbadosv AnguillaCFU Caribbean Cup qualification | 7–1 | CFU Caribbean Cup qualification |
| 2006-09-22 |  Antigua and BarbudavBarbadosCFU Caribbean Cup qualification | 1–3 | CFU Caribbean Cup qualification |
| 2006-09-20 | BarbadosvSaint Kitts and NevisCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 2001-04-08 | BarbadosvArubaCFU Caribbean Cup qualification | 5–2 | CFU Caribbean Cup qualification |
| 2001-04-06 | SurinamevBarbadosCFU Caribbean Cup qualification | 2–2 | CFU Caribbean Cup qualification |
| 2001-04-04 | Barbadosv GrenadaCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 1999-03-14 |  GuadeloupevBarbadosCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1999-03-12 | BarbadosvDominicaCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 1999-03-10 | BarbadosvAntigua and BarbudaCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 1999-03-06 | Barbadosv GuyanaCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 1999-02-28 | GuyanavBarbadosCFU Caribbean Cup qualification | 2–2 | CFU Caribbean Cup qualification |
| 1998-03-20 |  MartiniquevBarbadosCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 1998-03-18 |  Saint LuciavBarbadosCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 1997-04-06 | GuyanavBarbadosCFU Caribbean Cup qualification | 0–2 | CFU Caribbean Cup qualification |
| 1997-04-02 | BarbadosvGrenadaCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1996-04-28 | Barbadosv JamaicaCFU Caribbean Cup qualification | 2–0 p | CFU Caribbean Cup qualification |
| 1996-04-24 | JamaicavBarbadosCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |
| 1995-05-07 | Saint LuciavBarbadosCFU Caribbean Cup qualification | 2–1 | CFU Caribbean Cup qualification |
| 1995-04-30 | BarbadosvSaint LuciaCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1995-04-02 | GuyanavBarbadosCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 1995-03-26 | BarbadosvGuyanaCFU Caribbean Cup qualification | 3–0 | CFU Caribbean Cup qualification |
| 1994-01-27 | BarbadosvGrenadaCFU Caribbean Cup qualification | 3–2 | CFU Caribbean Cup qualification |
| 1994-01-23 | Barbadosv Puerto RicoCFU Caribbean Cup qualification | 0–1 | CFU Caribbean Cup qualification |
| 1993-03-14 | GuyanavBarbadosCFU Caribbean Cup qualification | 0–3 | CFU Caribbean Cup qualification |
| 1993-03-12 |  Cayman IslandsvBarbadosCFU Caribbean Cup qualification | 1–6 | CFU Caribbean Cup qualification |
| 1993-03-11 | Puerto RicovBarbadosCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1992-03-06 | BarbadosvCuraçaoplayed as Netherlands AntillesCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1990-05-26 | BermudavBarbadosCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1990-04-29 | BarbadosvAntigua and BarbudaCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1990-04-15 | BarbadosvSaint LuciaCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1987-12-06 |  Trinidad and TobagovBarbadosCFU Caribbean Cup qualification | 5–1 | CFU Caribbean Cup qualification |
| 1987-11-29 | BarbadosvTrinidad and TobagoCFU Caribbean Cup qualification | 0–4 | CFU Caribbean Cup qualification |
| 1983-05-08 | GuyanavBarbadosCFU Caribbean Cup qualification | 2–0 | CFU Caribbean Cup qualification |