 |
 |
|
|
| 1st(1st leg) | Akademija Pandev | - | FK Osogovo | 3:0 | ||
| 2nd (2nd leg) | FK Osogovo | - | Akademija Pandev | 1:4 | ||
| 1st(1st leg): 25/09/2019 14:30 | 2nd (2nd leg): 30/10/2019 12:30 | Winner: Akademija Pandev | ||||
| 1st(1st leg) | FK Bregalnica Štip | - | Makedonija GP | 1:0 | ||
| 2nd (2nd leg) | Makedonija GP | - | FK Bregalnica Štip | 0:0 | ||
| 1st(1st leg): 25/09/2019 14:30 | 2nd (2nd leg): 30/10/2019 12:30 | Winner: FK Bregalnica Štip | ||||
| 1st(1st leg) | KF Shkupi | - | Sileks Kratovo | 0:0 | ||
| 2nd (2nd leg) | Sileks Kratovo | - | KF Shkupi | 1:1 | ||
| 1st(1st leg): 25/09/2019 14:30 | 2nd (2nd leg): 30/10/2019 12:30 | Winner: KF Shkupi | ||||
| 1st(1st leg) | FK Pelister | - | FK Rabotnički | 1:1 | ||
| 2nd (2nd leg) | FK Rabotnički | - | FK Pelister | 4:0 | ||
| 1st(1st leg): 25/09/2019 14:30 | 2nd (2nd leg): 30/10/2019 12:30 | Winner: FK Rabotnički | ||||
| 1st(1st leg) | GFK Tikvesh | - | FK Renova | 0:2 | ||
| 2nd (2nd leg) | FK Renova | - | GFK Tikvesh | 1:1 | ||
| 1st(1st leg): 25/09/2019 14:30 | 2nd (2nd leg): 31/10/2019 12:30 | Winner: FK Renova | ||||
| 1st(1st leg) | FK Labuništa | - | FK Ohrid | 2:0 | ||
| 2nd (2nd leg) | FK Ohrid | - | FK Labuništa | 2:3 | ||
| 1st(1st leg): 25/09/2019 14:30 | 2nd (2nd leg): 30/10/2019 12:30 | Winner: FK Labuništa | ||||
| 1st(1st leg) | FK Borec | - | FC Struga | 0:0 | ||
| 2nd (2nd leg) | FC Struga | - | FK Borec | 1:0 | ||
| 1st(1st leg): 25/09/2019 14:30 | 2nd (2nd leg): 30/10/2019 12:30 | Winner: FC Struga | ||||
| 1st(1st leg) | Vardar Skopje | - | KF Shkëndija 79 | 2:2 | ||
| 2nd (2nd leg) | KF Shkëndija 79 | - | Vardar Skopje | 1:0 | ||
| 1st(1st leg): 25/09/2019 14:30 | 2nd (2nd leg): 30/10/2019 12:30 | Winner: KF Shkëndija 79 | ||||
