| tuesday september 3 - 22:45 |  FC West Bay #4 | 0-1 | 3 | League of Anguilla | SF | | |
| wednesday august 21 - 05:23 | FC The Farrington #2 | 0-0 | 1 | League of Anguilla | SK | | |
| tuesday august 20 - 22:17 | Stoney Ground #7 | 0-0 | 1 | Friendly | SK | | |
| monday august 19 - 09:34 | FC Long Bay | 2-6 | 0 | Friendly | GK | | |
| sunday august 18 - 01:39 | FC The Farrington #3 | 2-3 | 3 | Friendly | GK | | |
| saturday august 17 - 09:30 | Island Harbour #7 | 1-4 | 0 | Friendly | GK | | |
| friday august 16 - 20:26 | FC George Hill #2 | 3-1 | 0 | Friendly | GK | | |
| thursday august 15 - 09:46 | FC The Valley #3 | 3-0 | 3 | Friendly | SK | | |
| wednesday august 14 - 08:33 | The Valley City FC | 6-0 | 0 | Friendly | SK | | |
| tuesday august 13 - 09:22 | FC The Valley #11 | 4-1 | 3 | Friendly | SK | | |
