| tuesday october 1 - 05:29 |  The Farrington #8 | 3-1 | 0 | League of Anguilla [2] | DCB | |  |
| monday september 30 - 04:25 | FC The Valley #3 | 2-2 | 1 | League of Anguilla [2] | RB | | |
| sunday september 29 - 22:31 | Stoney Ground #7 | 1-0 | 0 | League of Anguilla [2] | RB | | |
| saturday september 28 - 04:50 | FC George Hill #2 | 1-7 | 0 | League of Anguilla [2] | CB | | |
| friday september 27 - 04:15 | FC The Valley #10 | 4-2 | 3 | League of Anguilla [2] | CB | | |
| thursday september 26 - 14:44 | FC The Valley #11 | 6-1 | 0 | League of Anguilla [2] | DCB | | |
| wednesday september 25 - 04:45 | FC The Farrington #3 | 2-3 | 0 | League of Anguilla [2] | DCB | | |
| tuesday september 24 - 13:20 | Harogate | 4-1 | 0 | League of Anguilla [2] | RB | | |
| monday september 23 - 19:24 | George Hill #8 | 2-0 | 0 | League of Anguilla [2] | DCB | | |
| saturday september 21 - 04:19 | The Farrington #8 | 1-5 | 0 | League of Anguilla [2] | CB | | |
| thursday september 19 - 04:17 | Stoney Ground #7 | 1-2 | 0 | League of Anguilla [2] | RB | | |
| wednesday september 18 - 20:48 | FC George Hill #2 | 2-0 | 0 | League of Anguilla [2] | CB | | |
| tuesday september 17 - 01:43 | FC The Valley #10 | 1-0 | 0 | League of Anguilla [2] | RB | | |
| monday september 16 - 04:26 | FC The Valley #11 | 2-2 | 1 | League of Anguilla [2] | RB | | |
| sunday september 15 - 01:27 | FC The Farrington #3 | 2-1 | 0 | League of Anguilla [2] | RB | | |
| saturday september 14 - 04:39 | Harogate | 3-3 | 1 | League of Anguilla [2] | RB | | |
| friday september 13 - 04:18 | George Hill #8 | 1-1 | 1 | League of Anguilla [2] | RB | | |
| thursday september 12 - 05:48 | The Farrington #8 | 0-0 | 1 | League of Anguilla [2] | SB | | |
| wednesday september 11 - 04:34 | FC The Valley #3 | 0-1 | 0 | League of Anguilla [2] | RB | | |
| tuesday september 10 - 22:42 | Stoney Ground #7 | 2-1 | 0 | League of Anguilla [2] | SB | | |
| monday september 9 - 04:42 | FC George Hill #2 | 1-0 | 3 | League of Anguilla [2] | RB | | |
| sunday september 8 - 04:40 | FC The Valley #10 | 2-0 | 3 | League of Anguilla [2] | RB | | |
| saturday september 7 - 14:23 | FC The Valley #11 | 3-3 | 1 | League of Anguilla [2] | SB | | |
| sunday september 1 - 04:33 | The Farrington #8 | 0-2 | 0 | League of Anguilla [2] | RB | |  |
| saturday august 31 - 14:49 | FC The Valley #3 | 0-0 | 1 | League of Anguilla [2] | SB | | |
