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| H (Match allé) | Portmore United | - | UWI Pelicans | 1:2 | ||
| R (match retour) | UWI Pelicans | - | Portmore United | 0:2 ap | ||
| H (Match allé): 07.05.2017 22:00 | R (match retour): 28.05.2017 22:00 | vainqueur: Portmore United | ||||
| H (Match allé) | Arnett Gardens | - | Humble Lions | 2:1 | ||
| R (match retour) | Humble Lions | - | Arnett Gardens | 0:1 | ||
| H (Match allé): 09.05.2017 03:00 | R (match retour): 21.05.2017 22:00 | vainqueur: Arnett Gardens | ||||
