| 1. Jornada | 11.08.2019 | Vardar Skopje | - | Makedonija GP | 0:2 |  |
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| 2. Jornada | 18.08.2019 | FK Borec | - | Vardar Skopje | 0:0 | ||||
| 11. Jornada | 23.10.2019 | Vardar Skopje | - | FK Borec | 2:0 | ||||
| 13. Jornada | 03.11.2019 | Vardar Skopje | - | FK Renova | 2:0 | ||||
| 14. Jornada | 09.11.2019 | FC Struga | - | Vardar Skopje | 2:1 | ||||
| 16. Jornada | 27.11.2019 | Sileks Kratovo | - | Vardar Skopje | 2:2 | |
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| 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 | ||||
| 20. Jornada | 22.02.2020 | FK Borec | - | Vardar Skopje | 0:1 |
Macedonia del Norte