World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group D |
 | 10.06.2025 |  | Guyana | | Montserrat |  | |
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World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group D |
 | 04.06.2025 |  | Montserrat | | Belize |  | |
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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 |