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| 1st(1st leg) | Mount Pleasant Academy | - | Portmore United | 1:2 | ||
| 2nd (2nd leg) | Portmore United | - | Mount Pleasant Academy | 1:1 | ||
| 1st(1st leg): 08/04/2019 23:30 | 2nd (2nd leg): 16/04/2019 02:35 | Winner: Portmore United | ||||
| 1st(1st leg) | Cavalier FC | - | Waterhouse FC | 0:2 | ||
| 2nd (2nd leg) | Waterhouse FC | - | Cavalier FC | 1:0 | ||
| 1st(1st leg): 09/04/2019 02:35 | 2nd (2nd leg): 15/04/2019 23:30 | Winner: Waterhouse FC | ||||
