| 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 | ||||
| 4. Jornada | 31.08.2019 | FK Borec | - | KF Shkëndija 79 | 1:0 | ||||
| 5. Jornada | 14.09.2019 | Makedonija GP | - | FK Borec | 3:1 | ||||
| 6. Jornada | 18.09.2019 | Sileks Kratovo | - | FK Borec | 3:0 | ||||
| 7. Jornada | 21.09.2019 | FK Borec | - | FK Rabotnički | 1:1 | ||||
| 8. Jornada | 29.09.2019 | FK Renova | - | FK Borec | 2:1 | ||||
| 11. Jornada | 23.10.2019 | Vardar Skopje | - | FK Borec | 2:0 |
Macedonia del Norte