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| 1st(1st leg) | UWI Pelicans | - | Mount Pleasant Academy | 2:2 | ||
| 2nd (2nd leg) | Mount Pleasant Academy | - | UWI Pelicans | 1:0 | ||
| 1st(1st leg): 24/03/2019 22:00 | 2nd (2nd leg): 31/03/2019 21:30 | Winner: Mount Pleasant Academy | ||||
| 1st(1st leg) | Arnett Gardens | - | Cavalier FC | 0:3 | ||
| 2nd (2nd leg) | Cavalier FC | - | Arnett Gardens | 0:0 | ||
| 1st(1st leg): 25/03/2019 01:00 | 2nd (2nd leg): 02/04/2019 02:35 | Winner: Cavalier FC | ||||
