1. Round | 11/08/2019 | Vardar Skopje | - | Makedonija GP | 0:2 | ||||
2. Round | 18/08/2019 | FK Borec | - | Vardar Skopje | 0:0 | ||||
3. Round | 24/08/2019 | Vardar Skopje | - | FK Rabotnički | 2:0 | ||||
4. Round | 01/09/2019 | FK Renova | - | Vardar Skopje | 0:1 | ||||
5. Round | 14/09/2019 | Vardar Skopje | - | FC Struga | 3:0 | ||||
6. Round | 18/09/2019 | KF Shkupi | - | Vardar Skopje | 1:2 | ||||
7. Round | 22/09/2019 | Vardar Skopje | - | Sileks Kratovo | 3:0 | ||||
8. Round | 29/09/2019 | Vardar Skopje | - | Akademija Pandev | 1:0 | ||||
11. Round | 23/10/2019 | Vardar Skopje | - | FK Borec | 2:0 | ||||
16. Round | 27/11/2019 | Sileks Kratovo | - | Vardar Skopje | 2:2 | ||||
17. Round | 01/12/2019 | Akademija Pandev | - | Vardar Skopje | 0:3 | ||||
18. Round | 08/12/2019 | Vardar Skopje | - | KF Shkëndija 79 | 2:2 |