| Today - 20:19 |  Saint Mary's | 4-0 | 3 | League of Anguilla | SF | | |
| thursday october 17 - 05:15 | FC The Farrington #2 | 0-1 | 3 | League of Anguilla | SF | | |
| tuesday october 15 - 20:50 | FC George Hill #2 | 1-1 | 1 | League of Anguilla | SF | | |
| saturday october 12 - 20:45 | FC Long Bay | 7-2 | 3 | League of Anguilla | SF | | |
| friday october 11 - 06:51 | Nyctophobia | 8-0 | 0 | Friendly | SF | | |
| thursday october 10 - 20:27 | George Hill United FC | 1-1 | 1 | Friendly | SF | | |
| wednesday october 9 - 13:19 | Harogate | 1-2 | 3 | Friendly | SF | | |
| tuesday october 8 - 20:20 | FC Long Bay | 4-1 | 3 | Friendly | SF | | |
| monday october 7 - 01:51 | FC The Farrington #3 | 2-5 | 3 | Friendly | SF | | |
| sunday october 6 - 20:50 | FC George Hill #2 | 4-0 | 3 | Friendly | SF | | |
| saturday october 5 - 01:43 | FC The Valley #10 | 2-3 | 3 | Friendly | SF | | |
| friday october 4 - 20:18 | Stoney Ground #6 | 1-0 | 3 | Friendly | SF | | |
