World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group D |
 | 10.06.2025 | | Guyana | – | Montserrat | | 3:0 (2:0) |
| Leonora |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group D |
| 04.06.2025 | | Montserrat | – | Belize | | 1:0 (1:0) |
| Trinidad and Tobago, Couva |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group D |
| 09.06.2024 | | Montserrat | – | Panama | | 1:3 (0:1) |
| Nicaragua, Managua |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group D |
| 05.06.2024 | | Nicaragua | – | Montserrat | | 4:1 (2:1) |
| Managua |
World Cup 2022, Qualifying tournament, CONCACAF, Group A |
| 08.06.2021 | | Grenada | – | Montserrat | | 1:2 (0:0) |
| Saint George's |
World Cup 2022, Qualifying tournament, CONCACAF, Group A |
| 02.06.2021 | | Montserrat | – | US Virgin Islands | | 4:0 (1:0) |
| Dominican Republic, San Cristóbal |
World Cup 2022, Qualifying tournament, CONCACAF, Group A |
| 28.03.2021 | | Montserrat | – | El Salvador | | 1:1 (0:1) |
| Curaçao, Willemstad |
World Cup 2022, Qualifying tournament, CONCACAF, Group A |
| 24.03.2021 | | Antigua and Barbuda | – | Montserrat | | 2:2 (2:2) * |
| Curaçao, Willemstad |
World Cup 2018, Qualifying tournament, CONCACAF, First Round |
| 31.03.2015 | | Montserrat | – | Curaçao | | 2:2 (0:1) |
| Plymouth |
World Cup 2018, Qualifying tournament, CONCACAF, First Round |
| 27.03.2015 | | Curaçao | – | Montserrat | | 2:1 (2:1) |
| Willemstad |
World Cup 2014, Qualifying tournament, CONCACAF, First Round |
| 17.07.2011 | | Belize | – | Montserrat | | 3:1 (1:0) |
| Honduras, San Pedro Sula |
World Cup 2014, Qualifying tournament, CONCACAF, First Round |
| 15.06.2011 | | Montserrat | – | Belize | | 2:5 (1:1) |
| Trinidad and Tobago, Couva |
World Cup 2010, Qualifying tournament, CONCACAF, First Round |
| 26.03.2008 | | Suriname | – | Montserrat | | 7:1 (2:0) |
| Trinidad and Tobago, Macoya |
World Cup 2006, Qualifying tournament, CONCACAF, First Round |
| 21.03.2004 | | Montserrat | – | Bermuda | | 0:7 (0:4) |
| Plymouth |
World Cup 2006, Qualifying tournament, CONCACAF, First Round |
| 29.02.2004 | | Bermuda | – | Montserrat | | 13:0 (6:0) |
| Hamilton |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 1, Group 3 |
| 19.03.2000 | | Montserrat | – | Dominican Republic | | 1:3 (0:1) |
| Trinidad and Tobago, Port of Spain |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 1, Group 3 |
| 05.03.2000 | | Dominican Republic | – | Montserrat | | 3:0 (3:0) |
| San Cristóbal |
