| 1. Round | 09/08/2020 | Makedonija GP | - | FK Rabotnički | 2:1 | ||||
| 2. Round | 15/08/2020 | FK Rabotnički | - | FK Belasica | 2:0 | ||||
| 3. Round | 23/08/2020 | FK Pelister | - | FK Rabotnički | 0:0 |  |
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| 4. Round | 29/08/2020 | FK Rabotnički | - | Vardar Skopje | 1:1 | ||||
| 5. Round | 13/09/2020 | FK Renova | - | FK Rabotnički | 0:1 |  |
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| 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 | ||||
| 10. Round | 25/10/2020 | KF Shkëndija 79 | - | FK Rabotnički | 1:1 | ||||
| 13. Round | 29/11/2020 | FK Belasica | - | FK Rabotnički | 2:2 | ||||
| 14. Round | 02/12/2020 | FK Rabotnički | - | FK Pelister | 1:0 | |
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| 15. Round | 06/12/2020 | Vardar Skopje | - | FK Rabotnički | 0:0 | ||||
| 21. Round | 03/03/2021 | FK Rabotnički | - | KF Shkëndija 79 | 0:0 | ||||
| 22. Round | 07/03/2021 | KF Shkupi | - | FK Rabotnički | 0:2 | ||||
| 23. Round | 13/03/2021 | FK Rabotnički | - | FK AP Brera Strumica | 0:2 | ||||
| 24. Round | 20/03/2021 | FK Belasica | - | FK Rabotnički | 1:1 | |
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| 25. Round | 04/04/2021 | FK Rabotnički | - | FK Borec | 2:1 | |
North Macedonia
Bulgaria