| 1. Jornada | 10.08.2019 | KF Shkupi | - | FK Borec | 2:0 | ||||
| 2. Jornada | 18.08.2019 | FK Borec | - | Vardar Skopje | 0:0 | ||||
| 3. Jornada | 25.08.2019 | FK AP Brera Strumica | - | FK Borec | 2:0 |  |
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| 5. Jornada | 14.09.2019 | Makedonija GP | - | FK Borec | 3:1 | ||||
| 6. Jornada | 18.09.2019 | Sileks Kratovo | - | FK Borec | 3:0 |  |
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| 9. Jornada | 05.10.2019 | FK Borec | - | FC Struga | 3:2 | ||||
| 12. Jornada | 27.10.2019 | FK Borec | - | FK AP Brera Strumica | 1:0 | ||||
| 17. Jornada | 01.12.2019 | FK Borec | - | FK Renova | 1:0 |
Macedonia del Norte