| 4. Jornada | 31.08.2019 | FK Rabotnički | - | FK AP Brera Strumica | 1:2 | ||||
| 5. Jornada | 13.09.2019 | FK AP Brera Strumica | - | FK Renova | 2:0 |  |
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| 6. Jornada | 18.09.2019 | FC Struga | - | FK AP Brera Strumica | 0:0 | ||||
| 10. Jornada | 18.10.2019 | KF Shkëndija 79 | - | FK AP Brera Strumica | 0:1 | ||||
| 14. Jornada | 09.11.2019 | FK Renova | - | FK AP Brera Strumica | 1:1 | |
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| 15. Jornada | 24.11.2019 | FK AP Brera Strumica | - | FC Struga | 1:1 | ||||
| 17. Jornada | 01.12.2019 | FK AP Brera Strumica | - | Vardar Skopje | 0:3 | ||||
| 20. Jornada | 23.02.2020 | Makedonija GP | - | FK AP Brera Strumica | 1:0 |  |
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| 23. Jornada | 11.03.2020 | FK AP Brera Strumica | - | FK Renova | 0:1 |
Macedonia del Norte