| thursday december 12 - 08:19 |  The Valley #9 | 3-1 | 0 | League of Anguilla | DM | | |
| wednesday december 11 - 22:34 | Nyctophobia | 1-10 | 0 | League of Anguilla | DM | |  |
| tuesday december 10 - 22:22 | FC George Hill #2 | 4-0 | 3 | League of Anguilla | DM | | |
| sunday december 8 - 21:22 |  FC Bridgetown #20 | 4-0 | 0 | North American League Q2 | SM | | |
| sunday december 8 - 02:38 | FC Shoal Bay Village #3 | 1-1 | 1 | League of Anguilla | LM | | |
| friday december 6 - 22:30 | FC The Farrington #2 | 4-0 | 3 | League of Anguilla | SM | | |
| friday december 6 - 21:21 | FC Bridgetown #20 | 4-2 | 3 | North American League Q2 | DM | | |
| tuesday december 3 - 09:31 | Stoney Ground #6 | 1-2 | 3 | League of Anguilla | DM | | |
| monday december 2 - 01:18 | FC The Farrington #3 | 1-4 | 3 | Friendly | DM | | |
| sunday december 1 - 22:47 | Harogate | 4-3 | 3 | Friendly | LM | | |
| saturday november 30 - 08:33 | George Hill #8 | 1-2 | 3 | Friendly | DM | | |
| friday november 29 - 22:34 | FC The Farrington #2 | 1-1 | 1 | Friendly | DM | | |
| thursday november 28 - 08:48 | The Valley #9 | 3-2 | 0 | Friendly | DM | | |
| wednesday november 27 - 22:31 | FC The Valley #3 | 3-0 | 3 | Friendly | CM | | |
| tuesday november 26 - 05:32 | Saint Mary's | 0-3 | 3 | Friendly | DM | | |
| monday november 25 - 22:37 | Stoney Ground #6 | 4-1 | 3 | Friendly | DM | | |
