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| 1st(1st leg) | Harbour View | - | Montego Bay United FC | 2:2 | ||
| 2nd (2nd leg) | Montego Bay United FC | - | Harbour View | 1:0 | ||
| 1st(1st leg): 08/05/2014 01:00 | 2nd (2nd leg): 11/05/2014 21:00 | Winner: Montego Bay United FC | ||||
| 1st(1st leg) | Waterhouse FC | - | Arnett Gardens | 3:3 | ||
| 2nd (2nd leg) | Arnett Gardens | - | Waterhouse FC | 1:2 | ||
| 1st(1st leg): 09/05/2014 01:00 | 2nd (2nd leg): 13/05/2014 02:30 | Winner: Waterhouse FC | ||||
