| 1. Round | 07/08/2022 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
| 2. Round | 14/08/2022 | KF Shkëndija 79 | - | Sileks Kratovo | 1:1 | ||||
| 3. Round | 21/08/2022 | Sileks Kratovo | - | FK Skopje | 3:1 |  |
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| 4. Round | 27/08/2022 | Sileks Kratovo | - | FK AP Brera Strumica | 1:1 | |
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| 5. Round | 31/08/2022 | FC Struga | - | Sileks Kratovo | 2:1 | ||||
| 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 | ||||
| 12. Round | 26/10/2022 | FK Rabotnički | - | Sileks Kratovo | 0:1 | |
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| 13. Round | 30/10/2022 | Sileks Kratovo | - | KF Shkëndija 79 | 1:1 | |
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| 14. Round | 05/11/2022 | FK Skopje | - | Sileks Kratovo | 0:0 | |
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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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| 18. Round | 11/12/2022 | Sileks Kratovo | - | Makedonija GP | 1:3 |
Serbia