| saturday november 2 - 08:28 |  FC The Valley #10 | 0-2 | 0 | League of Anguilla [2] | S | | |
| friday november 1 - 04:35 | Bassa | 1-2 | 3 | League of Anguilla [2] | S |  | |
| thursday october 31 - 08:25 | FC The Valley #3 | 1-0 | 3 | League of Anguilla [2] | S | | |
| wednesday october 30 - 16:16 | FC George Hill #7 | 2-1 | 0 | League of Anguilla [2] | S | | |
| tuesday october 29 - 08:16 | FC The Valley #11 | 2-3 | 0 | League of Anguilla [2] | S | | |
| sunday october 27 - 08:18 | FC Shoal Bay Village #3 | 1-1 | 1 | League of Anguilla [2] | S | | |
| saturday october 26 - 01:23 | FC The Farrington #3 | 0-2 | 3 | League of Anguilla [2] | S | | |
| friday october 25 - 05:21 | The Farrington #8 | 0-2 | 3 | League of Anguilla [2] | S | | |
| wednesday october 23 - 08:32 | Harogate | 3-3 | 1 | League of Anguilla [2] | S | | |
| tuesday october 22 - 01:22 | FC The Valley #10 | 0-2 | 3 | League of Anguilla [2] | S | | |
| monday october 21 - 08:29 | Bassa | 2-2 | 1 | League of Anguilla [2] | S | | |
| sunday october 20 - 14:17 | FC The Valley #3 | 0-1 | 3 | League of Anguilla [2] | RF | | |
| saturday october 19 - 19:15 | FC George Hill #7 | 1-0 | 3 | League of Anguilla [2] | RF | |  |
| friday october 18 - 14:00 |  Jwaneng Galaxy FC | 0-10 | 0 | Friendly | S | | |
| thursday october 17 - 14:46 | FC The Valley #11 | 3-6 | 3 | League of Anguilla [2] | S | | |
| tuesday october 15 - 02:23 | FC Shoal Bay Village #3 | 1-0 | 0 | League of Anguilla [2] | S | | |
| monday october 14 - 03:32 | FC The Valley #3 | 3-1* | 0 | Cup | S | | |
| saturday october 12 - 19:47 | FC The Farrington #3 | 3-1 | 3 | League of Anguilla [2] | S | | |
| friday october 11 - 19:28 | The Valley #9 | 2-0 | 3 | Friendly | S | | |
| thursday october 10 - 20:27 | Island Harbour #7 | 1-1 | 1 | Friendly | S | | |
| wednesday october 9 - 19:21 | FC The Valley #3 | 3-0 | 3 | Friendly | S | | |
| tuesday october 8 - 06:32 | Nyctophobia | 8-0 | 0 | Friendly | S | | |
| monday october 7 - 22:50 | FC West Bay #4 | 1-0 | 0 | Friendly | S | | |
| sunday october 6 - 19:45 | Harogate | 3-0 | 3 | Friendly | S | | |
| saturday october 5 - 22:42 | FC Long Bay | 1-0 | 0 | Friendly | S | | |
