| Ayer - 14:50 |  FC Anna's Retreat | 1-2 | 0 | Liga de San Kitts y Nevis [2] | SF | | |
| lunes julio 29 - 13:23 | Basseterre #8 | 5-0 | 0 | Liga de San Kitts y Nevis [2] | RW | | |
| domingo julio 28 - 14:32 | Newcastle | 0-4 | 0 | Liga de San Kitts y Nevis [2] | LW | | |
| sábado julio 27 - 04:39 | FC Basseterre | 5-2 | 0 | Liga de San Kitts y Nevis [2] | LW | | |
| viernes julio 26 - 14:40 | Basseterre #10 | 0-2 | 0 | Liga de San Kitts y Nevis [2] | RW | | |
| viernes julio 26 - 11:03 | AS Trinity Crayfish Sub21 | 8-0 | 0 | Liga Sub21 | SF | | |
| miércoles julio 24 - 14:26 | FC East End | 3-2 | 3 | Liga de San Kitts y Nevis [2] | SF | | |
| lunes julio 22 - 16:27 | FC Anna's Retreat | 2-3 | 3 | Liga de San Kitts y Nevis [2] | SF | | |
| sábado julio 20 - 14:44 | Basseterre #8 | 6-2 | 3 | Liga de San Kitts y Nevis [2] | SM | | |
| viernes julio 19 - 20:27 | Newcastle | 2-0 | 0 | Liga de San Kitts y Nevis [2] | S | | |
| viernes julio 19 - 11:02 | AS Trinity Crayfish Sub21 | 4-0 | 0 | Liga Sub21 | SF | | |
| jueves julio 18 - 14:15 | FC Basseterre | 1-0 | 3 | Liga de San Kitts y Nevis [2] | S | | |
| miércoles julio 17 - 18:21 | Basseterre #10 | 3-1 | 0 | Liga de San Kitts y Nevis [2] | S | | |
| lunes julio 15 - 14:30 | Monkey Hill #2 | 4-0 | 3 | Liga de San Kitts y Nevis [2] | S |  | |
| domingo julio 14 - 16:32 | FC East End | 1-1 | 1 | Liga de San Kitts y Nevis [2] | S | | |
| jueves julio 11 - 14:49 | FC Anna's Retreat | 3-2 | 3 | Liga de San Kitts y Nevis [2] | S | | |
| jueves julio 11 - 01:04 | Monkey Hill #2 Sub21 | 0-6 | 3 | Liga Sub21 | S | | |
| miércoles julio 10 - 01:02 | Liberia Sub21 | 5-1 | 0 | Liga Sub21 | SF | | |
| domingo julio 7 - 09:04 | Cube Football Club Sub21 | 3-3 | 1 | Liga Sub21 | RCF | | |
| viernes julio 5 - 14:38 | Basseterre #10 | 2-1 | 3 | Liga de San Kitts y Nevis [2] | SF | | |
| martes julio 2 - 23:11 | Basseterre #8 | 0-3 | 3 | Copa | SF | | |
| lunes julio 1 - 14:01 | AS Trinity Crayfish Sub21 | 0-8 | 0 | Liga Sub21 | SF | | |
| domingo junio 30 - 14:35 | FC East End | 5-4 | 3 | Liga de San Kitts y Nevis [2] | SF | | |
| sábado junio 29 - 14:05 | Basseterre #8 Sub21 | 6-0 | 3 | Liga Sub21 [2] | SF | | |
| jueves junio 27 - 14:31 | Newcastle | 2-2 | 1 | Amistoso | SF | | |
