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| H (Match allé) | UWI Pelicans | - | Mount Pleasant Academy | 2:2 | ||
| R (match retour) | Mount Pleasant Academy | - | UWI Pelicans | 1:0 | ||
| H (Match allé): 24.03.2019 23:00 | R (match retour): 31.03.2019 22:30 | vainqueur: Mount Pleasant Academy | ||||
| H (Match allé) | Arnett Gardens | - | Cavalier FC | 0:3 | ||
| R (match retour) | Cavalier FC | - | Arnett Gardens | 0:0 | ||
| H (Match allé): 25.03.2019 02:00 | R (match retour): 02.04.2019 03:35 | vainqueur: Cavalier FC | ||||
