| thursday october 17 - 01:23 |  FC The Valley #10 | 4-2 | 0 | League of Anguilla [2] | DM | |  |
| tuesday october 15 - 02:23 | George Hill United FC | 1-0 | 3 | League of Anguilla [2] | CM |  |  |
| saturday october 12 - 04:47 | Bassa | 1-2 | 3 | League of Anguilla [2] | CM | | |
| friday october 11 - 20:18 | FC George Hill #2 | 0-3 | 3 | Friendly | LM | | |
| thursday october 10 - 02:20 | FC The Valley #10 | 4-1 | 3 | Friendly | DM | | |
| wednesday october 9 - 09:50 | Stoney Ground #6 | 2-2 | 1 | Friendly | LM | | |
| tuesday october 8 - 02:20 | FC The Farrington #2 | 0-0 | 1 | Friendly | DM | | |
| monday october 7 - 05:39 | Saint Mary's | 1-2 | 3 | Friendly | LM | | |
| sunday october 6 - 02:45 | FC West Bay #4 | 1-1 | 1 | Friendly | DM | | |
| friday october 4 - 04:28 | Bassa | 1-2 | 3 | Friendly | AM | | |
