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| 1st(1st leg) | Portmore United | - | UWI Pelicans | 1:2 | ||
| 2nd (2nd leg) | UWI Pelicans | - | Portmore United | 0:2 aet | ||
| 1st(1st leg): 07/05/2017 21:00 | 2nd (2nd leg): 28/05/2017 21:00 | Winner: Portmore United | ||||
| 1st(1st leg) | Arnett Gardens | - | Humble Lions | 2:1 | ||
| 2nd (2nd leg) | Humble Lions | - | Arnett Gardens | 0:1 | ||
| 1st(1st leg): 09/05/2017 02:00 | 2nd (2nd leg): 21/05/2017 21:00 | Winner: Arnett Gardens | ||||
