| 1. Jornada | 10.08.2019 | KF Shkupi | - | FK Borec | 2:0 | ||||
| 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 |  |
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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 | |
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| 10. Jornada | 19.10.2019 | FK Borec | - | KF Shkupi | 2:1 | ||||
| 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 | |
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| 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 | |
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| 20. Jornada | 22.02.2020 | FK Borec | - | Vardar Skopje | 0:1 | |
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| 22. Jornada | 08.03.2020 | FK Borec | - | KF Shkëndija 79 | 4:2 | |
Macedonia del Norte