| 4. Round | 31/08/2019 | FK Rabotnički | - | FK AP Brera Strumica | 1:2 |  |
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| 7. Round | 22/09/2019 | FK AP Brera Strumica | - | KF Shkupi | 0:0 | ||||
| 10. Round | 18/10/2019 | KF Shkëndija 79 | - | FK AP Brera Strumica | 0:1 | ||||
| 13. Round | 02/11/2019 | FK AP Brera Strumica | - | FK Rabotnički | 1:1 | ||||
| 14. Round | 09/11/2019 | FK Renova | - | FK AP Brera Strumica | 1:1 | |
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| 18. Round | 08/12/2019 | Sileks Kratovo | - | FK AP Brera Strumica | 3:1 | ||||
| 23. Round | 11/03/2020 | FK AP Brera Strumica | - | FK Renova | 0:1 |
North Macedonia