| CONCACAF Championship U20 | 2024/02/28 01:00 | Nicaragua U20 v Anguilla U20 | L | 5-0 |
| CONCACAF Championship U20 | 2024/02/23 22:00 | Cuba U20 v Anguilla U20 | L | 13-0 |
| CONCACAF Championship U20 | 2021/11/13 20:00 | Belize U20 v Anguilla U20 | L | 4-0 |
| CONCACAF Championship U20 | 2021/11/11 20:00 | Anguilla U20 v Saint-Martin U20 | D | 2-2 |
| CONCACAF Championship U20 | 2024/02/27 22:00 | Britse Maagdeneilanden - U20 v Belize U20 | W | 4-3 |
| CONCACAF Championship U20 | 2024/02/25 22:00 | Britse Maagdeneilanden - U20 v Cuba U20 | L | 1-2 |
| CONCACAF Championship U20 | 2024/02/24 01:00 | Nicaragua U20 v Britse Maagdeneilanden - U20 | L | 8-0 |
| CONCACAF Championship U20 | 2021/11/13 20:00 | Dominica U20 v Britse Maagdeneilanden - U20 | W | 0-1 |