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| U | Metalurg Skopje | - | Mladost Carev Dvor | niet gespeeld | ||
| R | Mladost Carev Dvor | - | Metalurg Skopje | niet gespeeld | ||
| U: 21.09.2016 | R: 12.10.2016 | Winnaars: Metalurg Skopje | ||||
| U | Akademija Pandev | - | KF Shkupi | 0:1 (0:0) | ||
| R | KF Shkupi | - | Akademija Pandev | 3:1 | ||
| U: 21.09.2016 15:30 | R: 12.10.2016 14:30 | Winnaars: KF Shkupi | ||||
| U | FK Pelister | - | FK Renova | 2:0 (2:0) | ||
| R | FK Renova | - | FK Pelister | 3:1 (3:0) | ||
| U: 21.09.2016 15:30 | R: 19.10.2016 14:30 | Winnaars: FK Pelister | ||||
| U | FK Vlazrimi 77 | - | Vardar Skopje | 1:3 (1:0) | ||
| R | Vardar Skopje | - | FK Vlazrimi 77 | 2:0 (1:0) | ||
| U: 21.09.2016 15:30 | R: 19.10.2016 14:30 | Winnaars: Vardar Skopje | ||||
| U | Sileks Kratovo | - | FK Turnovo | 2:1 (1:0) | ||
| R | FK Turnovo | - | Sileks Kratovo | 3:3 (2:2) | ||
| U: 21.09.2016 15:30 | R: 12.10.2016 14:30 | Winnaars: Sileks Kratovo | ||||
| U | FK Bregalnica Štip | - | FK Teteks | 4:0 (2:0) | ||
| R | FK Teteks | - | FK Bregalnica Štip | 1:2 (0:0) | ||
| U: 21.09.2016 15:30 | R: 12.10.2016 14:30 | Winnaars: FK Bregalnica Štip | ||||
| U | FK Novaci 2005 | - | FK Pobeda Junior | 1:2 (0:0) | ||
| R | FK Pobeda Junior | - | FK Novaci 2005 | 5:0 | ||
| U: 21.09.2016 15:30 | R: 12.10.2016 14:30 | Winnaars: FK Pobeda Junior | ||||
| U | FK Rabotnički | - | KF Shkëndija 79 | 0:2 (0:0) | ||
| R | KF Shkëndija 79 | - | FK Rabotnički | 0:0 (0:0) | ||
| U: 21.09.2016 15:30 | R: 19.10.2016 14:30 | Winnaars: KF Shkëndija 79 | ||||
