| 1. Jornada | 09.08.2020 | FK Belasica | - | Sileks Kratovo | 0:6 |  |
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| 2. Jornada | 14.08.2020 | Sileks Kratovo | - | FK Pelister | 2:2 | ||||
| 3. Jornada | 23.08.2020 | Vardar Skopje | - | Sileks Kratovo | 0:4 | ||||
| 4. Jornada | 31.08.2020 | Sileks Kratovo | - | FK Renova | 3:1 | ||||
| 6. Jornada | 20.09.2020 | Sileks Kratovo | - | FK Borec | 1:2 | ||||
| 7. Jornada | 27.09.2020 | FK AP Brera Strumica | - | Sileks Kratovo | 1:0 | |
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| 8. Jornada | 03.10.2020 | KF Shkëndija 79 | - | Sileks Kratovo | 1:1 | ||||
| 9. Jornada | 18.10.2020 | Sileks Kratovo | - | FK Rabotnički | 4:3 | ||||
| 10. Jornada | 24.10.2020 | KF Shkupi | - | Sileks Kratovo | 1:0 | |
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| 11. Jornada | 08.11.2020 | Sileks Kratovo | - | Makedonija GP | 0:3 | ||||
| 12. Jornada | 22.11.2020 | Sileks Kratovo | - | FK Belasica | 0:1 | ||||
| 13. Jornada | 29.11.2020 | FK Pelister | - | Sileks Kratovo | 1:2 | ||||
| 14. Jornada | 02.12.2020 | Sileks Kratovo | - | Vardar Skopje | 1:0 | ||||
| 15. Jornada | 06.12.2020 | FK Renova | - | Sileks Kratovo | 0:0 | ||||
| 16. Jornada | 09.12.2020 | Sileks Kratovo | - | FC Struga | 0:0 | ||||
| 17. Jornada | 13.12.2020 | FK Borec | - | Sileks Kratovo | 2:0 | ||||
| 18. Jornada | 16.12.2020 | Sileks Kratovo | - | FK AP Brera Strumica | 1:2 |
Macedonia del Norte