| 4. Jornada | 31.08.2019 | FK Borec | - | KF Shkëndija 79 | 1:0 | ||||
| 5. Jornada | 14.09.2019 | Makedonija GP | - | FK Borec | 3:1 |  |
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| 6. Jornada | 18.09.2019 | Sileks Kratovo | - | FK Borec | 3:0 | ||||
| 7. Jornada | 21.09.2019 | FK Borec | - | FK Rabotnički | 1:1 | |
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| 8. Jornada | 29.09.2019 | FK Renova | - | FK Borec | 2:1 | ||||
| 9. Jornada | 05.10.2019 | FK Borec | - | FC Struga | 3:2 | ||||
| 10. Jornada | 19.10.2019 | FK Borec | - | KF Shkupi | 2:1 | ||||
| 11. Jornada | 23.10.2019 | Vardar Skopje | - | FK Borec | 2:0 | ||||
| 12. Jornada | 27.10.2019 | FK Borec | - | FK AP Brera Strumica | 1:0 | ||||
| 13. Jornada | 03.11.2019 | KF Shkëndija 79 | - | FK Borec | 4:0 | ||||
| 14. Jornada | 09.11.2019 | FK Borec | - | Makedonija GP | 1:1 | ||||
| 15. Jornada | 24.11.2019 | FK Borec | - | Sileks Kratovo | 0:0 | ||||
| 16. Jornada | 27.11.2019 | FK Rabotnički | - | FK Borec | 2:1 | |
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| 17. Jornada | 01.12.2019 | FK Borec | - | FK Renova | 1:0 | ||||
| 18. Jornada | 08.12.2019 | FC Struga | - | FK Borec | 1:1 |
Macedonia del Norte