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