| 4. Jornada | 31.08.2019 | FK Borec | - | KF Shkëndija 79 | 1:0 | ||||
| 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 |  |
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| 18. Jornada | 08.12.2019 | FC Struga | - | FK Borec | 1:1 | ||||
| 21. Jornada | 01.03.2020 | FK AP Brera Strumica | - | FK Borec | 0:0 | |
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| 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