| thursday october 17 - 05:15 |  Island Harbour #7 | 0-1 | 0 | League of Anguilla | LM | | |
| tuesday october 15 - 22:41 | FC Long Bay | 1-4 | 3 | League of Anguilla | DM | | |
| saturday october 12 - 05:17 | Stoney Ground #6 | 4-2 | 3 | League of Anguilla | LM | |  |
| friday october 11 - 09:28 | Stoney Ground #6 | 2-1 | 0 | Friendly | LM | | |
| thursday october 10 - 05:38 | FC West Bay #4 | 2-0 | 3 | Friendly | LM | | |
| wednesday october 9 - 05:35 | Saint Mary's | 5-0 | 3 | Friendly | LM | | |
| tuesday october 8 - 02:20 | FC Shoal Bay Village #3 | 0-0 | 1 | Friendly | LM | | |
| sunday october 6 - 04:49 | Bassa | 2-3 | 3 | Friendly | LM | | |
| saturday october 5 - 05:38 | FC The Valley #11 | 6-0 | 3 | Friendly | LM | | |
| friday october 4 - 08:45 | The Valley #9 | 2-1 | 0 | Friendly | LM | | |
