| 1. Round | 09/08/2020 | Makedonija GP | - | FK Rabotnički | 2:1 |  |
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| 2. Round | 15/08/2020 | FK Rabotnički | - | FK Belasica | 2:0 | ||||
| 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 | |
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| 8. Round | 03/10/2020 | FK Rabotnički | - | FK AP Brera Strumica | 0:0 | ||||
| 9. Round | 18/10/2020 | Sileks Kratovo | - | FK Rabotnički | 4:3 | ||||
| 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 | |
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| 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 | ||||
| 18. Round | 16/12/2020 | FK Rabotnički | - | FK Borec | 2:1 | ||||
| 19. Round | 13/02/2021 | FK AP Brera Strumica | - | FK Rabotnički | 0:1 | ||||
| 26. Round | 10/04/2021 | FK Rabotnički | - | FK Pelister | 3:1 | ||||
| 31. Round | 01/05/2021 | Vardar Skopje | - | FK Rabotnički | 1:3 |
North Macedonia