| 1. Jornada | 10.08.2019 | KF Shkupi | - | FK Borec | 2:0 | ||||
| 2. Jornada | 18.08.2019 | FK Borec | - | Vardar Skopje | 0:0 |  |
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| 3. Jornada | 25.08.2019 | FK AP Brera Strumica | - | FK Borec | 2:0 | ||||
| 4. Jornada | 31.08.2019 | FK Borec | - | KF Shkëndija 79 | 1:0 | ||||
| 6. Jornada | 18.09.2019 | Sileks Kratovo | - | FK Borec | 3:0 | ||||
| 13. Jornada | 03.11.2019 | KF Shkëndija 79 | - | FK Borec | 4:0 | ||||
| 14. Jornada | 09.11.2019 | FK Borec | - | Makedonija GP | 1:1 | |
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| 15. Jornada | 24.11.2019 | FK Borec | - | Sileks Kratovo | 0:0 | |
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| 16. Jornada | 27.11.2019 | FK Rabotnički | - | FK Borec | 2:1 | ||||
| 17. Jornada | 01.12.2019 | FK Borec | - | FK Renova | 1:0 | ||||
| 18. Jornada | 08.12.2019 | FC Struga | - | FK Borec | 1:1 | ||||
| 19. Jornada | 16.02.2020 | KF Shkupi | - | FK Borec | 2:0 | ||||
| 20. Jornada | 22.02.2020 | FK Borec | - | Vardar Skopje | 0:1 | ||||
| 21. Jornada | 01.03.2020 | FK AP Brera Strumica | - | FK Borec | 0:0 | ||||
| 22. Jornada | 08.03.2020 | FK Borec | - | KF Shkëndija 79 | 4:2 | ||||
| 23. Jornada | 11.03.2020 | Makedonija GP | - | FK Borec | 0:2 |
Macedonia del Norte