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| H (Match allé) | Waterhouse FC | - | Tivoli Gardens | 1:1 | ||
| R (match retour) | Tivoli Gardens | - | Waterhouse FC | 0:2 | ||
| H (Match allé): 23.04.2024 00:00 | R (match retour): 30.04.2024 03:00 | vainqueur: Waterhouse FC | ||||
| H (Match allé) | Arnett Gardens | - | Portmore United | 1:1 | ||
| R (match retour) | Portmore United | - | Arnett Gardens | 0:1 | ||
| H (Match allé): 23.04.2024 02:30 | R (match retour): 30.04.2024 00:00 | vainqueur: Arnett Gardens | ||||
