Caribbean Championship 2014, Qualifying tournament, Preliminary round, group 1 |
 | 03.06.2014 |  | Bonaire | – | Montserrat |  | 0:0 |
| Plymouth |
Caribbean Championship 2014, Qualifying tournament, Preliminary round, group 1 |
| 30.05.2014 | | Montserrat | – | US Virgin Islands |  | 1:0 (0:0) |
| Plymouth |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 3 |
| 09.09.2012 |  | British Virgin Islands | – | Montserrat | | 0:7 (0:3) |
| Fort-de-France |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 3 |
| 07.09.2012 |  | Martinique | – | Montserrat | | 5:0 (3:0) |
| Rivière-Pilote |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 3 |
| 05.09.2012 | | Montserrat | – | Suriname |  | 1:7 (0:5) |
| Le Lamentin |
Caribbean Championship 2010, Qualifying tournament, First Round, Group B |
| 10.10.2010 |  | Saint Kitts and Nevis | – | Montserrat | | 4:0 (3:0) |
| Kingstown |
Caribbean Championship 2010, Qualifying tournament, First Round, Group B |
| 08.10.2010 | | Montserrat | – | Barbados |  | 0:5 (0:2) |
| Kingstown |
Caribbean Championship 2010, Qualifying tournament, First Round, Group B |
| 06.10.2010 |  | Saint Vincent and Grenadines | – | Montserrat | | 7:0 (2:0) |
| Kingstown |
Caribbean Cup 2005, Qualifying tournament, Group F |
| 04.11.2004 |  | Saint Lucia | – | Montserrat | | 3:0 |
| Bassterre |
Caribbean Cup 2005, Qualifying tournament, Group F |
| 02.11.2004 | | Montserrat | – | Antigua and Barbuda |  | 4:5 (2:1) |
| Bassterre |
Caribbean Cup 2005, Qualifying tournament, Group F |
| 31.10.2004 | | Saint Kitts and Nevis | – | Montserrat | | 6:1 (3:0) |
| Bassterre |
Caribbean Cup 2001, Qualifying tournament, Preliminary round, group 1 |
| 08.02.2001 |  | Anguilla | – | Montserrat | | 4:1 (3:0) |
| Marigot |
Caribbean Cup 2001, Qualifying tournament, Preliminary round, group 1 |
| 06.02.2001 |  | Sint Maarten | – | Montserrat | | 3:1 (0:0) |
| Philipsburg |
Caribbean Cup 1999, Qualifying tournament, Preliminary round, group D |
| 07.02.1999 | | British Virgin Islands | – | Montserrat | | 3:0 (2:0) |
| Road Town |
Caribbean Cup 1999, Qualifying tournament, Preliminary round, group D |
| 05.02.1999 | | British Virgin Islands | – | Montserrat | | 3:1 (2:0) |
| Road Town |
Caribbean Cup 1995, Qualifying tournament, Group 4, Round 2 |
| 07.05.1995 | | Montserrat | – | Saint Vincent and Grenadines | | 0:11 |
| Woodlands |
Caribbean Cup 1995, Qualifying tournament, Group 4, Round 2 |
| 01.05.1995 | | Saint Vincent and Grenadines | – | Montserrat | | 9:0 |
| Kingstown |
Caribbean Cup 1995, Qualifying tournament, Group 4, Round 1 |
| 02.04.1995 | | Anguilla | – | Montserrat | | 0:1 |
| The Valley |
Caribbean Cup 1995, Qualifying tournament, Group 4, Round 1 |
| 26.03.1995 | | Montserrat | – | Anguilla | | 3:2 |
| Woodlands |
Caribbean Cup 1994, Qualifying tournament, Group 4 |
| 27.02.1994 |  | Dominica | – | Montserrat | | -:- |
| Bassterre |
Caribbean Cup 1994, Qualifying tournament, Group 4 |
| 25.02.1994 | | Antigua and Barbuda | – | Montserrat | | 8:0 |
| Bassterre |
Caribbean Cup 1994, Qualifying tournament, Group 4 |
| 23.02.1994 | | Saint Kitts and Nevis | – | Montserrat | | 9:1 |
| Bassterre |
Caribbean Cup 1992, Qualifying tournament, Group 4 |
| 19.04.1992 | | Montserrat | – | British Virgin Islands | | -:- |
| |
Caribbean Cup 1992, Qualifying tournament, Group 4 |
| 17.04.1992 | | Saint Kitts and Nevis | – | Montserrat | | 10:0 |
| |
Caribbean Cup 1992, Qualifying tournament, Group 4 |
| 15.04.1992 | | Antigua and Barbuda | – | Montserrat | | 5:0 |
| |
Caribbean Cup 1991, Qualifying tournament, Group 6 |
| 07.03.1991 | | Montserrat | – | Anguilla | | 1:1 |
| Castries |
Caribbean Cup 1991, Qualifying tournament, Group 6 |
| 05.03.1991 | | Saint Lucia | – | Montserrat | | 3:0 |
| Castries |
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