| thursday september 12 - 05:43 |  FC The Farrington #2 | 1-1 | 1 | League of Anguilla | DM | | |
| tuesday september 10 - 22:41 | Stoney Ground #6 | 2-0 | 3 | League of Anguilla | RM | | |
| monday september 9 - 16:34 | FC George Hill #7 | 0-2 | 3 | League of Anguilla | RM | | |
| saturday september 7 - 22:29 | FC West Bay #4 | 3-2 | 0 | League of Anguilla | RM | | |
| saturday august 31 - 02:15 | FC Shoal Bay Village #3 | 6-2 | 0 | League of Anguilla | DM | |  |
| friday august 30 - 09:46 | Stoney Ground #6 | 2-6 | 3 | League of Anguilla | RM | | |
| thursday august 29 - 22:24 | FC George Hill #7 | 1-0 | 3 | League of Anguilla | RM | |  |
| wednesday august 28 - 05:38 | Saint Mary's | 0-3 | 3 | League of Anguilla | DM | | |
| monday august 26 - 21:42 |  Isótopos de Hortaleza | 14-0 | 0 | North American League Q2 | RM | | |
| saturday august 24 - 03:40 | Isótopos de Hortaleza | 0-13 | 0 | North American League Q2 | DM | | |
| wednesday august 21 - 22:51 | The Valley City FC | 1-3 | 0 | League of Anguilla | RM | | |
| monday august 19 - 09:34 | Stoney Ground #6 | 2-6 | 3 | Friendly | RM | | |
| sunday august 18 - 22:37 | FC George Hill #7 | 1-0 | 3 | Friendly | RM | | |
| saturday august 17 - 05:48 | FC The Farrington #2 | 2-1 | 0 | Friendly | RM | | |
| friday august 16 - 22:33 | FC West Bay #4 | 3-3 | 1 | Friendly | RM | | |
| thursday august 15 - 19:31 | George Hill #8 | 1-1 | 1 | Friendly | RM | | |
| wednesday august 14 - 22:16 | Saint Mary's | 2-0 | 3 | Friendly | RM | | |
