| thursday april 11 - 08:26 |  The Valley City FC | 1-3 | 3 | League of Anguilla | SB | | |
| wednesday april 10 - 05:49 | FC Shoal Bay Village #3 | 7-0 | 3 | League of Anguilla | SB | | |
| tuesday april 9 - 05:36 | FC The Farrington #2 | 0-6 | 3 | League of Anguilla | DCB | | |
| monday april 8 - 05:45 | FC West Bay #4 | 6-0 | 3 | League of Anguilla | DCB | | |
| sunday april 7 - 20:48 | Island Harbour #7 | 0-8 | 3 | League of Anguilla | SB | | |
| saturday april 6 - 05:46 | Stoney Ground #6 | 10-0 | 3 | League of Anguilla | DCB | | |
| friday april 5 - 22:27 | FC Long Bay | 0-9 | 3 | League of Anguilla | SB | | |
| thursday april 4 - 05:30 | FC The Valley #10 | 8-0 | 3 | League of Anguilla | DCB | | |
| tuesday april 2 - 16:32 | FC George Hill #7 | 0-4 | 3 | League of Anguilla | SB | | |
| monday april 1 - 06:23 | The Valley City FC | 6-0 | 3 | League of Anguilla | DCB | | |
| sunday march 31 - 02:38 | FC Shoal Bay Village #3 | 0-6 | 3 | League of Anguilla | SB | | |
| friday march 29 - 06:21 | FC The Farrington #2 | 8-0 | 3 | League of Anguilla | CB |  | |
| thursday march 28 - 22:35 | FC West Bay #4 | 0-6 | 3 | League of Anguilla | CB | | |
| wednesday march 27 - 06:27 | Island Harbour #7 | 10-0 | 3 | League of Anguilla | SB | | |
| tuesday march 26 - 09:38 | Stoney Ground #6 | 0-10 | 3 | League of Anguilla | DCB | |  |
| monday march 25 - 06:18 | FC Long Bay | 7-0 | 3 | League of Anguilla | DCB | | |
| saturday march 23 - 01:28 | FC The Valley #10 | 0-8 | 3 | League of Anguilla | CB | | |
| thursday march 21 - 06:23 | FC George Hill #7 | 8-0 | 3 | League of Anguilla | CB | | |
| monday march 18 - 12:44 |  Caribbean Kings | 4-1 | 0 | North American Champions League Q1 | DCB | | |
| monday march 18 - 08:28 | The Valley City FC | 0-7 | 3 | League of Anguilla | DCB | | |
| sunday march 17 - 21:22 | Caribbean Kings | 0-3 | 0 | North American Champions League Q1 | DCB | | |
