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| H | Harbour View | - | Cavalier FC | 0:1 | ||
| R | Cavalier FC | - | Harbour View | 2:0 | ||
| H: 30.05.2023 00:00 | R: 05.06.2023 03:00 | Sieger: Cavalier FC | ||||
| H | Mount Pleasant Academy | - | Arnett Gardens | 2:2 | ||
| R | Arnett Gardens | - | Mount Pleasant Academy | 1:3 | ||
| H: 30.05.2023 02:30 | R: 05.06.2023 00:00 | Sieger: Mount Pleasant Academy | ||||
