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| H (Match allé) | Dunbeholden FC | - | Mount Pleasant Academy | 1:1 | ||
| R (match retour) | Mount Pleasant Academy | - | Dunbeholden FC | 3:0 | ||
| H (Match allé): 16.05.2023 00:00 | R (match retour): 23.05.2023 03:00 | vainqueur: Mount Pleasant Academy | ||||
| H (Match allé) | Humble Lions | - | Harbour View | 0:2 | ||
| R (match retour) | Harbour View | - | Humble Lions | 2:3 | ||
| H (Match allé): 16.05.2023 02:30 | R (match retour): 23.05.2023 00:00 | vainqueur: Harbour View | ||||
