| 2. Ronde | 18.08.2019 | FK Renova | - | FC Struga | 2:1 | ||||
| 4. Ronde | 31.08.2019 | FC Struga | - | KF Shkupi | 1:1 |  |
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| 5. Ronde | 14.09.2019 | Vardar Skopje | - | FC Struga | 3:0 | ||||
| 7. Ronde | 22.09.2019 | KF Shkëndija 79 | - | FC Struga | 2:0 | ||||
| 8. Ronde | 29.09.2019 | FC Struga | - | Makedonija GP | 0:2 | ||||
| 11. Ronde | 23.10.2019 | FC Struga | - | FK Renova | 1:0 | ||||
| 12. Ronde | 27.10.2019 | Sileks Kratovo | - | FC Struga | 1:0 | ||||
| 13. Ronde | 03.11.2019 | KF Shkupi | - | FC Struga | 0:0 | ||||
| 15. Ronde | 24.11.2019 | FK AP Brera Strumica | - | FC Struga | 1:1 | ||||
| 17. Ronde | 30.11.2019 | Makedonija GP | - | FC Struga | 1:1 | ||||
| 18. Ronde | 08.12.2019 | FC Struga | - | FK Borec | 1:1 | ||||
| 19. Ronde | 16.02.2020 | FC Struga | - | FK Rabotnički | 0:1 | ||||
| 20. Ronde | 23.02.2020 | FK Renova | - | FC Struga | 2:0 |  |
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| 22. Ronde | 08.03.2020 | FC Struga | - | KF Shkupi | 1:2 |  |
Noord-Macedonië