Anguilla's results this season.
| 10 Nov 2026 | Sint Maarten v Anguilla | 5-1 |
| 04 Oct 2026 | Aruba v Anguilla | 3-2 |
| 01 Oct 2026 | Anguilla v Antigua and Barbuda | 0-3 |
| 29 Sep 2026 | Anguilla v Aruba | 0-2 |
| 26 Sep 2026 | Antigua and Barbuda v Anguilla | 5-0 |
| 21 Sep 2026 | Dominica v Anguilla | 1-0 |