| 1. Round | 09/08/2020 | FK Belasica | - | Sileks Kratovo | 0:6 |  |
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| 2. Round | 14/08/2020 | Sileks Kratovo | - | FK Pelister | 2:2 | ||||
| 3. Round | 23/08/2020 | Vardar Skopje | - | Sileks Kratovo | 0:4 | ||||
| 4. Round | 31/08/2020 | Sileks Kratovo | - | FK Renova | 3:1 | ||||
| 5. Round | 12/09/2020 | FC Struga | - | Sileks Kratovo | 2:0 | ||||
| 6. Round | 20/09/2020 | Sileks Kratovo | - | FK Borec | 1:2 |  |
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| 7. Round | 27/09/2020 | FK AP Brera Strumica | - | Sileks Kratovo | 1:0 | ||||
| 8. Round | 03/10/2020 | KF Shkëndija 79 | - | Sileks Kratovo | 1:1 | |
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| 9. Round | 18/10/2020 | Sileks Kratovo | - | FK Rabotnički | 4:3 | |
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| 10. Round | 24/10/2020 | KF Shkupi | - | Sileks Kratovo | 1:0 | ||||
| 11. Round | 08/11/2020 | Sileks Kratovo | - | Makedonija GP | 0:3 | ||||
| 12. Round | 22/11/2020 | Sileks Kratovo | - | FK Belasica | 0:1 | ||||
| 13. Round | 29/11/2020 | FK Pelister | - | Sileks Kratovo | 1:2 | ||||
| 14. Round | 02/12/2020 | Sileks Kratovo | - | Vardar Skopje | 1:0 | ||||
| 15. Round | 06/12/2020 | FK Renova | - | Sileks Kratovo | 0:0 | ||||
| 16. Round | 09/12/2020 | Sileks Kratovo | - | FC Struga | 0:0 | ||||
| 17. Round | 13/12/2020 | FK Borec | - | Sileks Kratovo | 2:0 | ||||
| 18. Round | 16/12/2020 | Sileks Kratovo | - | FK AP Brera Strumica | 1:2 | |
Serbia