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| 1st(1st leg) | Harbour View | - | Cavalier FC | 0:1 | ||
| 2nd (2nd leg) | Cavalier FC | - | Harbour View | 2:0 | ||
| 1st(1st leg): 29/05/2023 23:00 | 2nd (2nd leg): 05/06/2023 02:00 | Winner: Cavalier FC | ||||
| 1st(1st leg) | Mount Pleasant Academy | - | Arnett Gardens | 2:2 | ||
| 2nd (2nd leg) | Arnett Gardens | - | Mount Pleasant Academy | 1:3 | ||
| 1st(1st leg): 30/05/2023 01:30 | 2nd (2nd leg): 04/06/2023 23:00 | Winner: Mount Pleasant Academy | ||||
