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| H (Match allé) | Harbour View | - | Cavalier FC | 0:1 | ||
| R (match retour) | Cavalier FC | - | Harbour View | 2:0 | ||
| H (Match allé): 30.05.2023 00:00 | R (match retour): 05.06.2023 03:00 | vainqueur: Cavalier FC | ||||
| H (Match allé) | Mount Pleasant Academy | - | Arnett Gardens | 2:2 | ||
| R (match retour) | Arnett Gardens | - | Mount Pleasant Academy | 1:3 | ||
| H (Match allé): 30.05.2023 02:30 | R (match retour): 05.06.2023 00:00 | vainqueur: Mount Pleasant Academy | ||||
