| Dominica Premier League | 04/20 20:00 | - | Bath Estate v Middleham United FC | W | 1-4 | |
| Dominica Premier League | 04/13 20:00 | - | Middleham United FC v Point Michel FC | W | 3-1 | |
| Dominica Premier League | 04/07 22:38 | - | We United FC v Middleham United FC | L | 4-0 | |
| Dominica Premier League | 08/12 22:24 | - | Middleham United FC v Point Michel FC | W | 1-0 | |
| Dominica Premier League | 07/12 22:30 | - | Middleham United FC v LA STARZ | D | Abandoned | |
| Dominica Premier League | 06/16 22:30 | - | Middleham United FC v Promex Harlem United SC | D | 1-1 | |
| Dominica Premier League | 05/05 22:30 | - | Middleham United FC v LA STARZ | W | 2-0 | |
| Dominica Premier League | 04/21 22:30 | - | Dublanc FC v Middleham United FC | L | 2-1 | |
| Dominica Premier League | 03/11 20:00 | - | 사우스 이스트 v Middleham United FC | W | 0-1 | |
| Dominica Premier League | 03/05 20:00 | - | East Central FC v Middleham United FC | D | 1-1 | |
| Dominica Premier League | 07/17 20:00 | - | East Central FC v Middleham United FC | W | 1-2 | |
| Dominica Premier League | 07/09 22:44 | - | Dublanc FC v Middleham United FC | L | 3-1 | |
| Dominica Premier League | 04/25 20:26 | - | Promex Harlem United SC v Middleham United FC | L | 3-1 | |
| Dominica Premier League | 12/08 20:06 | - | 사우스 이스트 v Middleham United FC | L | 1-0 |