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| H (Match allé) | Tivoli Gardens | - | Portmore United | 1:1 | ||
| R (match retour) | Portmore United | - | Tivoli Gardens | 2:1 | ||
| H (Match allé): 23.04.2017 22:00 | R (match retour): 30.04.2017 22:00 | vainqueur: Portmore United | ||||
| H (Match allé) | Arnett Gardens | - | Montego Bay United FC | 1:1 | ||
| R (match retour) | Montego Bay United FC | - | Arnett Gardens | 1:2 | ||
| H (Match allé): 25.04.2017 03:00 | R (match retour): 02.05.2017 03:00 | vainqueur: Arnett Gardens | ||||
