| 1. Jornada | 10.08.2019 | FC Struga | - | FK Rabotnički | 2:1 |  |
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| 2. Jornada | 18.08.2019 | FK Renova | - | FC Struga | 2:1 | |
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| 3. Jornada | 25.08.2019 | FC Struga | - | Sileks Kratovo | 2:1 | |
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| 4. Jornada | 31.08.2019 | FC Struga | - | KF Shkupi | 1:1 | ||||
| 5. Jornada | 14.09.2019 | Vardar Skopje | - | FC Struga | 3:0 | ||||
| 6. Jornada | 18.09.2019 | FC Struga | - | FK AP Brera Strumica | 0:0 | ||||
| 7. Jornada | 22.09.2019 | KF Shkëndija 79 | - | FC Struga | 2:0 | ||||
| 8. Jornada | 29.09.2019 | FC Struga | - | Makedonija GP | 0:2 | |
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| 9. Jornada | 05.10.2019 | FK Borec | - | FC Struga | 3:2 | ||||
| 10. Jornada | 19.10.2019 | FK Rabotnički | - | FC Struga | 1:2 | ||||
| 11. Jornada | 23.10.2019 | FC Struga | - | FK Renova | 1:0 |  |
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| 16. Jornada | 27.11.2019 | FC Struga | - | KF Shkëndija 79 | 2:1 | ||||
| 17. Jornada | 30.11.2019 | Makedonija GP | - | FC Struga | 1:1 |
Macedonia del Norte