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| U | Akademija Pandev | - | FK Osogovo | 3:0 | ||
| R | FK Osogovo | - | Akademija Pandev | 1:4 | ||
| U: 25.09.2019 15:30 | R: 30.10.2019 13:30 | Winnaars: Akademija Pandev | ||||
| U | FK Bregalnica Štip | - | Makedonija GP | 1:0 | ||
| R | Makedonija GP | - | FK Bregalnica Štip | 0:0 | ||
| U: 25.09.2019 15:30 | R: 30.10.2019 13:30 | Winnaars: FK Bregalnica Štip | ||||
| U | KF Shkupi | - | Sileks Kratovo | 0:0 | ||
| R | Sileks Kratovo | - | KF Shkupi | 1:1 | ||
| U: 25.09.2019 15:30 | R: 30.10.2019 13:30 | Winnaars: KF Shkupi | ||||
| U | FK Pelister | - | FK Rabotnički | 1:1 | ||
| R | FK Rabotnički | - | FK Pelister | 4:0 | ||
| U: 25.09.2019 15:30 | R: 30.10.2019 13:30 | Winnaars: FK Rabotnički | ||||
| U | GFK Tikvesh | - | FK Renova | 0:2 | ||
| R | FK Renova | - | GFK Tikvesh | 1:1 | ||
| U: 25.09.2019 15:30 | R: 31.10.2019 13:30 | Winnaars: FK Renova | ||||
| U | FK Labuništa | - | FK Ohrid | 2:0 | ||
| R | FK Ohrid | - | FK Labuništa | 2:3 | ||
| U: 25.09.2019 15:30 | R: 30.10.2019 13:30 | Winnaars: FK Labuništa | ||||
| U | FK Borec | - | FC Struga | 0:0 | ||
| R | FC Struga | - | FK Borec | 1:0 | ||
| U: 25.09.2019 15:30 | R: 30.10.2019 13:30 | Winnaars: FC Struga | ||||
| U | Vardar Skopje | - | KF Shkëndija 79 | 2:2 | ||
| R | KF Shkëndija 79 | - | Vardar Skopje | 1:0 | ||
| U: 25.09.2019 15:30 | R: 30.10.2019 13:30 | Winnaars: KF Shkëndija 79 | ||||
