| friday may 24 - 20:37 |  FC Charlestown | 2-1 | 3 | League of St. Kitts and Nevis [2] | AM | | |
| thursday may 23 - 14:47 | Phoenix T&C | 2-1 | 0 | League of St. Kitts and Nevis [2] | CM | | |
| wednesday may 22 - 16:22 | FC Anna's Retreat | 1-0 | 0 | League of St. Kitts and Nevis [2] | CM | | |
| monday may 20 - 16:19 | FC East End | 5-2 | 0 | League of St. Kitts and Nevis [2] | LM | | |
| sunday may 19 - 20:43 | Monkey Hill #2 | 3-0 | 3 | League of St. Kitts and Nevis [2] | AM |  | |
| sunday may 19 - 15:22 | Mansion | 1-0 | 3 | Cup | AM | | |
| saturday may 18 - 18:51 | FC Sadlers | 3-2 | 0 | League of St. Kitts and Nevis [2] | CM | | |
| friday may 17 - 20:38 | Basseterre #5 | 0-1 | 0 | League of St. Kitts and Nevis [2] | AM | | |
| thursday may 16 - 04:23 | FC Basseterre | 0-2 | 3 | League of St. Kitts and Nevis [2] | CM | | |
| tuesday may 14 - 20:24 | Basseterre #8 | 1-0 | 3 | League of St. Kitts and Nevis [2] | AM | | |
| sunday may 12 - 05:42 | FC Charlestown | 0-1 | 3 | League of St. Kitts and Nevis [2] | AM | | |
| saturday may 11 - 07:30 | Basseterre #5 | 0-1 | 3 | Cup | AM | | |
| thursday may 9 - 20:42 | Phoenix T&C | 2-2 | 1 | League of St. Kitts and Nevis [2] | CM | | |
| wednesday may 8 - 16:21 | FC East End | 3-2 | 0 | Friendly | CM | | |
| tuesday may 7 - 20:46 | Cube Football Club | 0-5 | 0 | Friendly | AM | | |
| monday may 6 - 01:48 | Monkey Hill #2 | 0-0 | 1 | Friendly | AM | | |
| sunday may 5 - 20:22 | Phoenix T&C | 3-0 | 3 | Friendly | AM | | |
| saturday may 4 - 06:51 | Mansion | 2-0 | 0 | Friendly | AM | | |
| friday may 3 - 20:18 | Basseterre #10 | 1-0 | 3 | Friendly | AM | | |
| thursday may 2 - 17:30 | FC Basseterre #7 | 2-0 | 0 | Friendly | AM | | |
| wednesday may 1 - 20:42 | Liberia | 0-8 | 0 | Friendly | AM | |  |
