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| H (Match allé) | KF Shkëndija 79 | - | FK Rabotnički | 1:1 | ||
| R (match retour) | FK Rabotnički | - | KF Shkëndija 79 | 2:2 (0:1) | ||
| H (Match allé): 04.12.2019 13:00 | R (match retour): 04.03.2020 14:00 | vainqueur: KF Shkëndija 79 | ||||
| H (Match allé) | KF Shkupi | - | Akademija Pandev | 0:1 | ||
| R (match retour) | Akademija Pandev | - | KF Shkupi | 1:1 (0:0) | ||
| H (Match allé): 04.12.2019 13:00 | R (match retour): 04.03.2020 14:00 | vainqueur: Akademija Pandev | ||||
| H (Match allé) | FC Struga | - | FK Renova | 0:0 | ||
| R (match retour) | FK Renova | - | FC Struga | 1:2 (1:1) | ||
| H (Match allé): 04.12.2019 13:00 | R (match retour): 04.03.2020 14:00 | vainqueur: FC Struga | ||||
| H (Match allé) | FK Bregalnica Štip | - | FK Labuništa | 1:0 | ||
| R (match retour) | FK Labuništa | - | FK Bregalnica Štip | 1:4 (0:3) | ||
| H (Match allé): 04.12.2019 16:30 | R (match retour): 04.03.2020 14:00 | vainqueur: FK Bregalnica Štip | ||||
