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| I | Mount Pleasant Academy | - | Portmore United | 1:2 | ||
| V | Portmore United | - | Mount Pleasant Academy | 1:1 | ||
| I: 09.04.2019 00:30 | V: 16.04.2019 03:35 | Campeones: Portmore United | ||||
| I | Cavalier FC | - | Waterhouse FC | 0:2 | ||
| V | Waterhouse FC | - | Cavalier FC | 1:0 | ||
| I: 09.04.2019 03:35 | V: 16.04.2019 00:30 | Campeones: Waterhouse FC | ||||
