| 1. Ronde | 09.08.2020 | Makedonija GP | - | FK Rabotnički | 2:1 |  |
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| 2. Ronde | 15.08.2020 | FK Rabotnički | - | FK Belasica | 2:0 | ||||
| 3. Ronde | 23.08.2020 | FK Pelister | - | FK Rabotnički | 0:0 | ||||
| 6. Ronde | 19.09.2020 | FK Rabotnički | - | FC Struga | 1:1 | ||||
| 7. Ronde | 26.09.2020 | FK Borec | - | FK Rabotnički | 0:0 | |
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| 8. Ronde | 03.10.2020 | FK Rabotnički | - | FK AP Brera Strumica | 0:0 | ||||
| 9. Ronde | 18.10.2020 | Sileks Kratovo | - | FK Rabotnički | 4:3 | |
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| 10. Ronde | 25.10.2020 | KF Shkëndija 79 | - | FK Rabotnički | 1:1 | |
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| 11. Ronde | 07.11.2020 | FK Rabotnički | - | KF Shkupi | 2:2 |  |
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| 13. Ronde | 29.11.2020 | FK Belasica | - | FK Rabotnički | 2:2 | |
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| 14. Ronde | 02.12.2020 | FK Rabotnički | - | FK Pelister | 1:0 | ||||
| 16. Ronde | 09.12.2020 | FK Rabotnički | - | FK Renova | 3:1 | |
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| 17. Ronde | 13.12.2020 | FC Struga | - | FK Rabotnički | 2:1 | ||||
| 18. Ronde | 16.12.2020 | FK Rabotnički | - | FK Borec | 2:1 |
Noord-Macedonië