| 1. Round | 07/08/2022 | Sileks Kratovo | - | FK Rabotnički | 2:0 |  |
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| 5. Round | 31/08/2022 | FC Struga | - | Sileks Kratovo | 2:1 | |
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| 6. Round | 04/09/2022 | Sileks Kratovo | - | GFK Tikvesh | 3:2 | |
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| 7. Round | 10/09/2022 | Makedonija GP | - | Sileks Kratovo | 0:1 | |
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| 9. Round | 02/10/2022 | KF Shkupi | - | Sileks Kratovo | 0:0 | ||||
| 10. Round | 09/10/2022 | Sileks Kratovo | - | FK Pobeda Junior | 0:3 | ||||
| 11. Round | 15/10/2022 | FK Bregalnica Štip | - | Sileks Kratovo | 2:3 | ||||
| 12. Round | 26/10/2022 | FK Rabotnički | - | Sileks Kratovo | 0:1 | ||||
| 13. Round | 30/10/2022 | Sileks Kratovo | - | KF Shkëndija 79 | 1:1 | |
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| 16. Round | 26/11/2022 | Sileks Kratovo | - | FC Struga | 1:2 | ||||
| 17. Round | 04/12/2022 | GFK Tikvesh | - | Sileks Kratovo | 0:2 | |
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| 20. Round | 26/02/2023 | Sileks Kratovo | - | KF Shkupi | 2:1 | ||||
| 22. Round | 08/03/2023 | Sileks Kratovo | - | FK Bregalnica Štip | 1:2 | |
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| 24. Round | 18/03/2023 | FK Pobeda Junior | - | Sileks Kratovo | 1:5 | |
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| 31. Round | 07/05/2023 | FC Struga | - | Sileks Kratovo | 3:0 | ||||
| 33. Round | 14/05/2023 | FK AP Brera Strumica | - | Sileks Kratovo | 2:2 | |
North Macedonia