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| U | Mount Pleasant Academy | - | Portmore United | 1:2 | ||
| R | Portmore United | - | Mount Pleasant Academy | 1:1 | ||
| U: 09.04.2019 00:30 | R: 16.04.2019 03:35 | Winnaars: Portmore United | ||||
| U | Cavalier FC | - | Waterhouse FC | 0:2 | ||
| R | Waterhouse FC | - | Cavalier FC | 1:0 | ||
| U: 09.04.2019 03:35 | R: 16.04.2019 00:30 | Winnaars: Waterhouse FC | ||||
