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| 1st(1st leg) | Humble Lions | - | Portmore United | 2:1 (0:0) | ||
| 2nd (2nd leg) | Portmore United | - | Humble Lions | 3:1 (2:0) | ||
| 1st(1st leg): 10/04/2016 21:30 | 2nd (2nd leg): 19/04/2016 02:40 | Winner: Portmore United | ||||
| 1st(1st leg) | Montego Bay United FC | - | Arnett Gardens | 2:1 (2:1) | ||
| 2nd (2nd leg) | Arnett Gardens | - | Montego Bay United FC | 2:2 (0:1, 2:1) aet | ||
| 1st(1st leg): 12/04/2016 02:30 | 2nd (2nd leg): 18/04/2016 00:00 | Winner: Montego Bay United FC | ||||
