| 1. Ronde | 10.08.2019 | FC Struga | - | FK Rabotnički | 2:1 | ||||
| 2. Ronde | 18.08.2019 | FK Renova | - | FC Struga | 2:1 |  |
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| 3. Ronde | 25.08.2019 | FC Struga | - | Sileks Kratovo | 2:1 | |
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| 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 | |
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| 6. Ronde | 18.09.2019 | FC Struga | - | FK AP Brera Strumica | 0:0 | |
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| 8. Ronde | 29.09.2019 | FC Struga | - | Makedonija GP | 0:2 | ||||
| 9. Ronde | 05.10.2019 | FK Borec | - | FC Struga | 3:2 | ||||
| 19. Ronde | 16.02.2020 | FC Struga | - | FK Rabotnički | 0:1 | ||||
| 20. Ronde | 23.02.2020 | FK Renova | - | FC Struga | 2:0 | ||||
| 21. Ronde | 29.02.2020 | FC Struga | - | Sileks Kratovo | 0:0 | |
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| 22. Ronde | 08.03.2020 | FC Struga | - | KF Shkupi | 1:2 | |
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| 23. Ronde | 11.03.2020 | Vardar Skopje | - | FC Struga | 1:0 |
Noord-Macedonië