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| U | FK Renova | - | FC Struga | 3:2 (0:2) | ||
| R | FC Struga | - | FK Renova | 2:2 (0:1) | ||
| U: 13.09.2017 15:30 | R: 18.10.2017 14:30 | Winnaars: FK Renova | ||||
| U | FK Rabotnički | - | KF Shkëndija 79 | 1:1 (0:1) | ||
| R | KF Shkëndija 79 | - | FK Rabotnički | 3:2 (1:0, 1:1) d.p. | ||
| U: 13.09.2017 15:30 | R: 18.10.2017 14:30 | Winnaars: KF Shkëndija 79 | ||||
| U | FK Bregalnica Štip | - | FK Pobeda Junior | 2:3 (1:0) | ||
| R | FK Pobeda Junior | - | FK Bregalnica Štip | 5:1 (1:0) | ||
| U: 13.09.2017 15:30 | R: 18.10.2017 14:30 | Winnaars: FK Pobeda Junior | ||||
| U | FK Pelister | - | FK Borec | 4:2 (0:0) | ||
| R | FK Borec | - | FK Pelister | 1:3 (0:0) | ||
| U: 13.09.2017 15:30 | R: 18.10.2017 14:30 | Winnaars: FK Pelister | ||||
| U | FK Skopje | - | FK Gorno Lisiče | 3:0 (0:0) | ||
| R | FK Gorno Lisiče | - | FK Skopje | 0:3 (0:1) | ||
| U: 13.09.2017 15:30 | R: 18.10.2017 14:30 | Winnaars: FK Skopje | ||||
| U | Sileks Kratovo | - | FK AP Brera Strumica | 1:0 (1:0) | ||
| R | FK AP Brera Strumica | - | Sileks Kratovo | 5:0 (1:0) | ||
| U: 13.09.2017 15:30 | R: 18.10.2017 14:30 | Winnaars: FK AP Brera Strumica | ||||
| U | FK Kožuf | - | FK Teteks | 2:2 (0:1) | ||
| R | FK Teteks | - | FK Kožuf | 3:2 (2:1) | ||
| U: 13.09.2017 15:30 | R: 17.10.2017 14:30 | Winnaars: FK Teteks | ||||
| U | Vardar Skopje | - | KF Shkupi | 1:1 (0:1) | ||
| R | KF Shkupi | - | Vardar Skopje | 0:2 (0:0) | ||
| U: 30.11.2017 13:00 | R: 17.12.2017 13:00 | Winnaars: Vardar Skopje | ||||
