| sunday may 12 - 21:45 |  Negril Beach | 2-3 | 0 | North American Champions League Q2 | CM | | |
| sunday may 12 - 20:32 |  Island Harbour #7 | 0-7 | 3 | League of Anguilla | AM | | |
| thursday may 9 - 15:35 |  FC Aguilares | 0-1 | 3 | North American Champions League Q1 | AM | | |
| thursday may 9 - 05:43 | FC Shoal Bay Village #3 | 8-0 | 3 | League of Anguilla | AM | | |
| wednesday may 8 - 21:48 | FC Aguilares | 2-0 | 3 | North American Champions League Q1 | AM | | |
| wednesday may 8 - 05:20 | The Valley City FC | 3-0 | 3 | Super Cup | AM | | |
| wednesday may 8 - 02:36 | FC Shoal Bay Village #3 | 0-3 | 3 | Friendly | SM | | |
| tuesday may 7 - 05:19 | George Hill #8 | 8-0 | 3 | Friendly | AM | |  |
| monday may 6 - 20:25 | FC George Hill #2 | 0-11 | 3 | Friendly | AM | | |
| sunday may 5 - 05:28 | FC The Farrington #2 | 9-0 | 3 | Friendly | AM | | |
| saturday may 4 - 05:42 | FC The Farrington #3 | 11-0 | 3 | Friendly | AM |  | |
| thursday may 2 - 05:44 | The Farrington #8 | 8-0 | 3 | Friendly | AM | | |
| wednesday may 1 - 22:32 | Stoney Ground #7 | 1-9 | 3 | Friendly | AM | | |
