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 |
Superclásico
Copa Newton
Copa Lipton
Copa Rosa
Copa Félix Bogado
Copa Carlos Dittborn
Copa Ramón Castilla
Copa Rio Branco
Copa Rodrigues Alves
Taça Bernardo O'Higgins
Copa Artigas
Copa Paz del Chaco
Copa del Pacífico
