| 1. Jornada | 11.08.2019 | Vardar Skopje | - | Makedonija GP | 0:2 | ||||
| 2. Jornada | 18.08.2019 | FK Borec | - | Vardar Skopje | 0:0 | ||||
| 3. Jornada | 24.08.2019 | Vardar Skopje | - | FK Rabotnički | 2:0 | ||||
| 4. Jornada | 01.09.2019 | FK Renova | - | Vardar Skopje | 0:1 | ||||
| 5. Jornada | 14.09.2019 | Vardar Skopje | - | FC Struga | 3:0 | ||||
| 6. Jornada | 18.09.2019 | KF Shkupi | - | Vardar Skopje | 1:2 |  |
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| 7. Jornada | 22.09.2019 | Vardar Skopje | - | Sileks Kratovo | 3:0 | ||||
| 8. Jornada | 29.09.2019 | Vardar Skopje | - | FK AP Brera Strumica | 1:0 | ||||
| 11. Jornada | 23.10.2019 | Vardar Skopje | - | FK Borec | 2:0 | |
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| 16. Jornada | 27.11.2019 | Sileks Kratovo | - | Vardar Skopje | 2:2 | ||||
| 17. Jornada | 01.12.2019 | FK AP Brera Strumica | - | Vardar Skopje | 0:3 | ||||
| 18. Jornada | 08.12.2019 | Vardar Skopje | - | KF Shkëndija 79 | 2:2 |
Macedonia del Norte