2. Round | 17/08/2019 | FK Rabotnički | - | KF Shkupi | 2:0 | ||||
3. Round | 24/08/2019 | Vardar Skopje | - | FK Rabotnički | 2:0 | ||||
4. Round | 31/08/2019 | FK Rabotnički | - | Akademija Pandev | 1:2 | ||||
5. Round | 14/09/2019 | KF Shkëndija 79 | - | FK Rabotnički | 3:0 | ||||
8. Round | 29/09/2019 | Sileks Kratovo | - | FK Rabotnički | 1:0 | ||||
9. Round | 04/10/2019 | FK Rabotnički | - | FK Renova | 1:0 | ||||
10. Round | 19/10/2019 | FK Rabotnički | - | FC Struga | 1:2 | ||||
12. Round | 26/10/2019 | FK Rabotnički | - | Vardar Skopje | 0:2 |