| 3. Round | 23/08/2020 | FK Pelister | - | FK Rabotnički | 0:0 | ||||
| 4. Round | 29/08/2020 | FK Rabotnički | - | Vardar Skopje | 1:1 | ||||
| 5. Round | 13/09/2020 | FK Renova | - | FK Rabotnički | 0:1 | ||||
| 6. Round | 19/09/2020 | FK Rabotnički | - | FC Struga | 1:1 | ||||
| 7. Round | 26/09/2020 | FK Borec | - | FK Rabotnički | 0:0 | ||||
| 8. Round | 03/10/2020 | FK Rabotnički | - | FK AP Brera Strumica | 0:0 | ||||
| 9. Round | 18/10/2020 | Sileks Kratovo | - | FK Rabotnički | 4:3 |  |
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| 10. Round | 25/10/2020 | KF Shkëndija 79 | - | FK Rabotnički | 1:1 | ||||
| 11. Round | 07/11/2020 | FK Rabotnički | - | KF Shkupi | 2:2 | ||||
| 12. Round | 22/11/2020 | FK Rabotnički | - | Makedonija GP | 1:3 | ||||
| 13. Round | 29/11/2020 | FK Belasica | - | FK Rabotnički | 2:2 | ||||
| 16. Round | 09/12/2020 | FK Rabotnički | - | FK Renova | 3:1 |
Serbia