| saturday september 7 - 09:35 |  Island Harbour #7 | 0-0 | 1 | League of Anguilla | SF | | |
| thursday september 5 - 05:21 | Saint Mary's | 2-1 | 0 | League of Anguilla | SF | | |
| wednesday september 4 - 09:35 | FC The Farrington #2 | 1-5 | 0 | League of Anguilla | S | | |
| tuesday september 3 - 22:45 | FC West Bay #4 | 0-1 | 3 | League of Anguilla | S | | |
| sunday september 1 - 09:18 | FC Shoal Bay Village #3 | 3-1 | 3 | League of Anguilla | SF | | |
| saturday august 31 - 23:27 | FC West Bay #4 | 2-1 | 3 | Cup | SM | | |
| saturday august 31 - 06:36 | Dong Xue Lian | 8-0 | 0 | League of Anguilla | LF | | |
| friday august 30 - 09:46 | FC Long Bay | 2-6 | 0 | League of Anguilla | SF | | |
| thursday august 29 - 08:28 | The Valley City FC | 5-0 | 0 | League of Anguilla | LF | | |
| wednesday august 28 - 09:29 | FC George Hill #7 | 0-1 | 0 | League of Anguilla | SM | | |
| monday august 26 - 20:40 | Island Harbour #7 | 4-3 | 0 | League of Anguilla | SF | | |
| saturday august 24 - 09:43 | Saint Mary's | 1-0 | 3 | League of Anguilla | SF | | |
| wednesday august 21 - 05:23 | FC The Farrington #2 | 0-0 | 1 | League of Anguilla | SF | | |
| tuesday august 20 - 22:17 | Stoney Ground #7 | 0-0 | 1 | Friendly | S | | |
| monday august 19 - 09:34 | FC Long Bay | 2-6 | 0 | Friendly | S |  | |
| sunday august 18 - 01:39 | FC The Farrington #3 | 2-3 | 3 | Friendly | SM | | |
| saturday august 17 - 09:30 | Island Harbour #7 | 1-4 | 0 | Friendly | S | | |
| friday august 16 - 20:26 | FC George Hill #2 | 3-1 | 0 | Friendly | SF | | |
| thursday august 15 - 09:46 | FC The Valley #3 | 3-0 | 3 | Friendly | SF | | |
| wednesday august 14 - 08:33 | The Valley City FC | 6-0 | 0 | Friendly | SF | | |
| tuesday august 13 - 09:22 | FC The Valley #11 | 4-1 | 3 | Friendly | S | | |
