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| I | Harbour View | - | Montego Bay United FC | 2:2 | ||
| V | Montego Bay United FC | - | Harbour View | 1:0 | ||
| I: 08.05.2014 02:00 | V: 11.05.2014 22:00 | Campeones: Montego Bay United FC | ||||
| I | Waterhouse FC | - | Arnett Gardens | 3:3 | ||
| V | Arnett Gardens | - | Waterhouse FC | 1:2 | ||
| I: 09.05.2014 02:00 | V: 13.05.2014 03:30 | Campeones: Waterhouse FC | ||||
