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| H (Match allé) | Harbour View | - | Montego Bay United FC | 2:2 | ||
| R (match retour) | Montego Bay United FC | - | Harbour View | 1:0 | ||
| H (Match allé): 08.05.2014 02:00 | R (match retour): 11.05.2014 22:00 | vainqueur: Montego Bay United FC | ||||
| H (Match allé) | Waterhouse FC | - | Arnett Gardens | 3:3 | ||
| R (match retour) | Arnett Gardens | - | Waterhouse FC | 1:2 | ||
| H (Match allé): 09.05.2014 02:00 | R (match retour): 13.05.2014 03:30 | vainqueur: Waterhouse FC | ||||
