World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group F |
 | 07.06.2025 |  | Anguilla | – | El Salvador |  | |
| |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group F |
| 04.06.2025 |  | Saint Vincent and Grenadines | – | Anguilla | | |
| |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group F |
| 11.06.2024 |  | Puerto Rico | – | Anguilla | | 8:0 (2:0) |
| Bayamón |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group F |
| 08.06.2024 | | Anguilla | – | Suriname |  | 0:4 (0:1) |
| The Valley Raymond E. Guishard Technical Centre |
World Cup 2026, Qualifying tournament, CONCACAF, First round |
| 26.03.2024 |  | Turks and Caicos Islands | – | Anguilla | | 1:1 aet
(1:1, 1:1),
pen. 3:4 |
| Providenciales |
World Cup 2026, Qualifying tournament, CONCACAF, First round |
| 22.03.2024 | | Anguilla | – | Turks and Caicos Islands | | 0:0 |
| The Valley Raymond E. Guishard Technical Centre |
World Cup 2022, Qualifying tournament, CONCACAF, Group D |
| 05.06.2021 | | Anguilla | – | Panama |  | 0:13 (0:4) |
| Panama, Ciudad de Panamá |
World Cup 2022, Qualifying tournament, CONCACAF, Group D |
| 02.06.2021 |  | Dominica | – | Anguilla | | 3:0 (3:0) |
| Dominican Republic, Santo Domingo de Guzmán |
World Cup 2022, Qualifying tournament, CONCACAF, Group D |
| 30.03.2021 |  | Barbados | – | Anguilla | | 1:0 (0:0) |
| Dominican Republic, Santo Domingo de Guzmán |
World Cup 2022, Qualifying tournament, CONCACAF, Group D |
| 27.03.2021 | | Anguilla | – | Dominican Republic |  | 0:6 (0:3) |
| USA, Fort Lauderdale |
World Cup 2018, Qualifying tournament, CONCACAF, First Round |
| 29.03.2015 | | Anguilla | – | Nicaragua |  | 0:3 (0:2) |
| The Valley |
World Cup 2018, Qualifying tournament, CONCACAF, First Round |
| 23.03.2015 | | Nicaragua | – | Anguilla | | 5:0 (4:0) |
| Managua |
World Cup 2014, Qualifying tournament, CONCACAF, First Round |
| 10.07.2011 | | Dominican Republic | – | Anguilla | | 4:0 (3:0) |
| San Cristóbal |
World Cup 2014, Qualifying tournament, CONCACAF, First Round |
| 08.07.2011 | | Anguilla | – | Dominican Republic | | 0:2 (0:2) |
| Dominican Republic, San Cristóbal |
World Cup 2010, Qualifying tournament, CONCACAF, First Round |
| 26.03.2008 | | Anguilla | – | El Salvador | | 0:4 (0:4) |
| USA, Washington |
World Cup 2010, Qualifying tournament, CONCACAF, First Round |
| 06.02.2008 | | El Salvador | – | Anguilla | | 12:0 (4:0) |
| San Salvador |
World Cup 2006, Qualifying tournament, CONCACAF, First Round |
| 21.03.2004 | | Anguilla | – | Dominican Republic | | 0:6 (0:2) |
| Santo Domingo de Guzmán |
World Cup 2006, Qualifying tournament, CONCACAF, First Round |
| 19.03.2004 | | Dominican Republic | – | Anguilla | | 0:0 |
| Santo Domingo de Guzmán |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 1, Group 3 |
| 19.03.2000 |  | Bahamas | – | Anguilla | | 2:1 (1:1) |
| Nassau |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 1, Group 3 |
| 05.03.2000 | | Anguilla | – | Bahamas | | 1:3 (0:3) |
| The Valley |
