| thursday september 12 - 05:48 |  The Farrington #8 | 0-0 | 1 | League of Anguilla [2] | AM | | |
| wednesday september 11 - 04:34 | FC The Valley #3 | 0-1 | 0 | League of Anguilla [2] | CM | | |
| tuesday september 10 - 22:42 | Stoney Ground #7 | 2-1 | 0 | League of Anguilla [2] | AM | | |
| monday september 9 - 04:42 | FC George Hill #2 | 1-0 | 3 | League of Anguilla [2] | AM | | |
| sunday september 8 - 04:40 | FC The Valley #10 | 2-0 | 3 | League of Anguilla [2] | AM | | |
| thursday september 5 - 04:16 | FC The Farrington #3 | 6-1 | 3 | League of Anguilla [2] | AM |  |  |
| wednesday september 4 - 13:18 | Harogate | 2-2 | 1 | League of Anguilla [2] | CM | | |
| tuesday september 3 - 19:45 | George Hill #8 | 0-1 | 3 | League of Anguilla [2] | AM | | |
| saturday august 31 - 14:49 | FC The Valley #3 | 0-0 | 1 | League of Anguilla [2] | LM | | |
| saturday august 31 - 12:34 | FC The Farrington #2 | 0-1 | 0 | Cup | AM | |  |
| friday august 30 - 04:38 | Stoney Ground #7 | 1-0 | 3 | League of Anguilla [2] | AM | | |
| thursday august 29 - 20:44 | FC George Hill #2 | 3-0 | 0 | League of Anguilla [2] | LM | | |
| wednesday august 28 - 01:37 | FC The Valley #10 | 1-1 | 1 | League of Anguilla [2] | DM | | |
| monday august 26 - 04:51 | FC The Valley #11 | 3-2 | 3 | League of Anguilla [2] | DM | | |
| wednesday august 21 - 04:18 | Harogate | 4-2 | 3 | League of Anguilla [2] | DM | | |
