| 2014-05-30 |  Montserratv United States Virgin IslandsCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 2012-09-09 |  British Virgin IslandsvMontserratCFU Caribbean Cup qualification | 0–7 | CFU Caribbean Cup qualification |
| 2012-09-07 |  MartiniquevMontserratCFU Caribbean Cup qualification | 5–0 | CFU Caribbean Cup qualification |
| 2012-09-05 | Montserratv SurinameCFU Caribbean Cup qualification | 1–7 | CFU Caribbean Cup qualification |
| 2010-10-10 |  Saint Kitts and NevisvMontserratCFU Caribbean Cup qualification | 4–0 | CFU Caribbean Cup qualification |
| 2010-10-08 | Montserratv BarbadosCFU Caribbean Cup qualification | 0–5 | CFU Caribbean Cup qualification |
| 2004-11-02 | Montserratv Antigua and BarbudaCFU Caribbean Cup qualification | 4–5 | CFU Caribbean Cup qualification |
| 2004-10-31 | Saint Kitts and NevisvMontserratCFU Caribbean Cup qualification | 6–1 | CFU Caribbean Cup qualification |
| 2001-02-08 |  AnguillavMontserratCFU Caribbean Cup qualification | 4–1 | CFU Caribbean Cup qualification |
| 2001-02-06 |  Saint MartinvMontserratCFU Caribbean Cup qualification | 3–1 | CFU Caribbean Cup qualification |
| 1999-02-07 | British Virgin IslandsvMontserratCFU Caribbean Cup qualification | 3–0 | CFU Caribbean Cup qualification |
| 1999-02-05 | British Virgin IslandsvMontserratCFU Caribbean Cup qualification | 3–1 | 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 |
| 1994-02-25 | Antigua and BarbudavMontserratCFU Caribbean Cup qualification | 8–0 | CFU Caribbean Cup qualification |
| 1994-02-23 | Saint Kitts and NevisvMontserratCFU Caribbean Cup qualification | 9–1 | CFU Caribbean Cup qualification |
| 1992-04-17 | Saint Kitts and NevisvMontserratCFU Caribbean Cup qualification | 10–0 | CFU Caribbean Cup qualification |
| 1992-04-15 | Antigua and BarbudavMontserratCFU Caribbean Cup qualification | 5–0 | CFU Caribbean Cup qualification |
| 1991-05-14 | AnguillavMontserratCFU Caribbean Cup qualification | 1–1 | CFU Caribbean Cup qualification |
| 1991-05-10 |  Saint LuciavMontserratCFU Caribbean Cup qualification | 3–0 | CFU Caribbean Cup qualification |