| 1. Round | 10/08/2019 | FK Renova | - | Sileks Kratovo | 1:0 |  |
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| 2. Round | 18/08/2019 | Sileks Kratovo | - | KF Shkëndija 79 | 1:0 |  |
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| 3. Round | 25/08/2019 | FC Struga | - | Sileks Kratovo | 2:1 | |
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| 4. Round | 31/08/2019 | Sileks Kratovo | - | Makedonija GP | 3:4 | |
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| 5. Round | 14/09/2019 | KF Shkupi | - | Sileks Kratovo | 1:0 | |
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| 6. Round | 18/09/2019 | Sileks Kratovo | - | FK Borec | 3:0 | |
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| 8. Round | 29/09/2019 | Sileks Kratovo | - | FK Rabotnički | 1:0 | ||||
| 9. Round | 05/10/2019 | FK AP Brera Strumica | - | Sileks Kratovo | 2:0 | ||||
| 10. Round | 19/10/2019 | Sileks Kratovo | - | FK Renova | 3:0 | ||||
| 11. Round | 23/10/2019 | KF Shkëndija 79 | - | Sileks Kratovo | 3:0 | ||||
| 12. Round | 27/10/2019 | Sileks Kratovo | - | FC Struga | 1:0 | ||||
| 13. Round | 03/11/2019 | Makedonija GP | - | Sileks Kratovo | 0:1 | |
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| 14. Round | 09/11/2019 | Sileks Kratovo | - | KF Shkupi | 1:0 | |
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| 15. Round | 24/11/2019 | FK Borec | - | Sileks Kratovo | 0:0 | ||||
| 16. Round | 27/11/2019 | Sileks Kratovo | - | Vardar Skopje | 2:2 | ||||
| 17. Round | 01/12/2019 | FK Rabotnički | - | Sileks Kratovo | 1:1 | ||||
| 18. Round | 08/12/2019 | Sileks Kratovo | - | FK AP Brera Strumica | 3:1 |
North Macedonia