| monday december 23 - 08:17 |  George Hill #8 | 0-2 | 3 | League of Anguilla [2] | SF | | |
| sunday december 22 - 14:16 | FC The Valley #3 | 5-2 | 3 | League of Anguilla [2] | SF |  | |
| saturday december 21 - 16:35 | FC George Hill #7 | 0-2 | 3 | League of Anguilla [2] | SF | | |
| wednesday december 18 - 22:15 | FC Long Bay | 2-4 | 3 | League of Anguilla [2] | SF | | |
| tuesday december 17 - 14:31 | Harogate | 5-6 | 0 | League of Anguilla [2] | SF | | |
| monday december 16 - 01:16 | FC The Farrington #3 | 1-5 | 3 | League of Anguilla [2] | SM | | |
| saturday december 14 - 14:47 | Bassa | 4-1 | 3 | League of Anguilla [2] | SM | | |
| friday december 13 - 22:51 | Stoney Ground #7 | 0-0 | 1 | League of Anguilla [2] | SM | | |
| friday december 13 - 15:21 | The Farrington #8 | 3-0 | 0 | Cup | SF | |  |
| monday december 2 - 14:37 | FC The Valley #3 | 0-1 | 3 | Friendly | SF | | |
| sunday december 1 - 14:43 | Saint Mary's | 3-0 | 3 | Friendly | SM | | |
| tuesday november 26 - 14:32 | Bassa | 6-2 | 3 | Friendly | SF | | |
| monday november 25 - 20:33 | FC George Hill #2 | 3-3 | 1 | Friendly | SF | | |
