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| U | FK Pelister | - | Sileks Kratovo | 1:0 (0:0) | ||
| R | Sileks Kratovo | - | FK Pelister | 1:2 (0:1) | ||
| U: 23.11.2016 13:30 | R: 07.12.2016 13:00 | Winnaars: FK Pelister | ||||
| U | Metalurg Skopje | - | Vardar Skopje | 1:4 (0:4) | ||
| R | Vardar Skopje | - | Metalurg Skopje | 4:1 (1:0) | ||
| U: 23.11.2016 13:30 | R: 07.12.2016 13:00 | Winnaars: Vardar Skopje | ||||
| U | KF Shkupi | - | KF Shkëndija 79 | 0:0 (0:0) | ||
| R | KF Shkëndija 79 | - | KF Shkupi | 4:0 (3:0) | ||
| U: 23.11.2016 13:30 | R: 07.12.2016 13:00 | Winnaars: KF Shkëndija 79 | ||||
| U | FK Pobeda Junior | - | FK Bregalnica Štip | 2:2 (1:1) | ||
| R | FK Bregalnica Štip | - | FK Pobeda Junior | 3:0 (1:0) | ||
| U: 23.11.2016 13:30 | R: 07.12.2016 13:00 | Winnaars: FK Bregalnica Štip | ||||
