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| 1st(1st leg) | Dunbeholden FC | - | Mount Pleasant Academy | 1:1 | ||
| 2nd (2nd leg) | Mount Pleasant Academy | - | Dunbeholden FC | 3:0 | ||
| 1st(1st leg): 15/05/2023 23:00 | 2nd (2nd leg): 23/05/2023 02:00 | Winner: Mount Pleasant Academy | ||||
| 1st(1st leg) | Humble Lions | - | Harbour View | 0:2 | ||
| 2nd (2nd leg) | Harbour View | - | Humble Lions | 2:3 | ||
| 1st(1st leg): 16/05/2023 01:30 | 2nd (2nd leg): 22/05/2023 23:00 | Winner: Harbour View | ||||
