| 10. Jornada | 25.10.2020 | FK Pelister | - | FC Struga | 1:1 | ||||
| 12. Jornada | 22.11.2020 | FK AP Brera Strumica | - | FK Pelister | 3:2 | ||||
| 13. Jornada | 29.11.2020 | FK Pelister | - | Sileks Kratovo | 1:2 | ||||
| 15. Jornada | 06.12.2020 | FK Pelister | - | KF Shkupi | 1:3 | ||||
| 16. Jornada | 09.12.2020 | Makedonija GP | - | FK Pelister | 2:1 |  |
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| 17. Jornada | 13.12.2020 | FK Pelister | - | FK Belasica | 1:0 |  |
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| 18. Jornada | 16.12.2020 | KF Shkëndija 79 | - | FK Pelister | 0:1 | ||||
| 19. Jornada | 21.02.2021 | Vardar Skopje | - | FK Pelister | 2:2 | ||||
| 28. Jornada | 18.04.2021 | FC Struga | - | FK Pelister | 3:0 |
Macedonia del Norte