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| H (Match allé) | Mount Pleasant Academy | - | Portmore United | 1:2 | ||
| R (match retour) | Portmore United | - | Mount Pleasant Academy | 1:1 | ||
| H (Match allé): 09.04.2019 00:30 | R (match retour): 16.04.2019 03:35 | vainqueur: Portmore United | ||||
| H (Match allé) | Cavalier FC | - | Waterhouse FC | 0:2 | ||
| R (match retour) | Waterhouse FC | - | Cavalier FC | 1:0 | ||
| H (Match allé): 09.04.2019 03:35 | R (match retour): 16.04.2019 00:30 | vainqueur: Waterhouse FC | ||||
