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| 1st(1st leg) | FK Renova | - | FC Struga | 3:2 (0:2) | ||
| 2nd (2nd leg) | FC Struga | - | FK Renova | 2:2 (0:1) | ||
| 1st(1st leg): 13/09/2017 14:30 | 2nd (2nd leg): 18/10/2017 13:30 | Winner: FK Renova | ||||
| 1st(1st leg) | FK Rabotnički | - | KF Shkëndija 79 | 1:1 (0:1) | ||
| 2nd (2nd leg) | KF Shkëndija 79 | - | FK Rabotnički | 3:2 (1:0, 1:1) pso | ||
| 1st(1st leg): 13/09/2017 14:30 | 2nd (2nd leg): 18/10/2017 13:30 | Winner: KF Shkëndija 79 | ||||
| 1st(1st leg) | FK Bregalnica Štip | - | FK Pobeda Junior | 2:3 (1:0) | ||
| 2nd (2nd leg) | FK Pobeda Junior | - | FK Bregalnica Štip | 5:1 (1:0) | ||
| 1st(1st leg): 13/09/2017 14:30 | 2nd (2nd leg): 18/10/2017 13:30 | Winner: FK Pobeda Junior | ||||
| 1st(1st leg) | FK Pelister | - | FK Borec | 4:2 (0:0) | ||
| 2nd (2nd leg) | FK Borec | - | FK Pelister | 1:3 (0:0) | ||
| 1st(1st leg): 13/09/2017 14:30 | 2nd (2nd leg): 18/10/2017 13:30 | Winner: FK Pelister | ||||
| 1st(1st leg) | FK Skopje | - | FK Gorno Lisiče | 3:0 (0:0) | ||
| 2nd (2nd leg) | FK Gorno Lisiče | - | FK Skopje | 0:3 (0:1) | ||
| 1st(1st leg): 13/09/2017 14:30 | 2nd (2nd leg): 18/10/2017 13:30 | Winner: FK Skopje | ||||
| 1st(1st leg) | Sileks Kratovo | - | Akademija Pandev | 1:0 (1:0) | ||
| 2nd (2nd leg) | Akademija Pandev | - | Sileks Kratovo | 5:0 (1:0) | ||
| 1st(1st leg): 13/09/2017 14:30 | 2nd (2nd leg): 18/10/2017 13:30 | Winner: Akademija Pandev | ||||
| 1st(1st leg) | FK Kožuf | - | FK Teteks | 2:2 (0:1) | ||
| 2nd (2nd leg) | FK Teteks | - | FK Kožuf | 3:2 (2:1) | ||
| 1st(1st leg): 13/09/2017 14:30 | 2nd (2nd leg): 17/10/2017 13:30 | Winner: FK Teteks | ||||
| 1st(1st leg) | Vardar Skopje | - | KF Shkupi | 1:1 (0:1) | ||
| 2nd (2nd leg) | KF Shkupi | - | Vardar Skopje | 0:2 (0:0) | ||
| 1st(1st leg): 30/11/2017 12:00 | 2nd (2nd leg): 17/12/2017 12:00 | Winner: Vardar Skopje | ||||
