| 1. Ronde | 07.08.2022 | Sileks Kratovo | - | FK Rabotnički | 2:0 |  |
|||
| 5. Ronde | 31.08.2022 | FC Struga | - | Sileks Kratovo | 2:1 | |
|||
| 6. Ronde | 04.09.2022 | Sileks Kratovo | - | GFK Tikvesh | 3:2 | |
|||
| 7. Ronde | 10.09.2022 | Makedonija GP | - | Sileks Kratovo | 0:1 | |
|||
| 9. Ronde | 02.10.2022 | KF Shkupi | - | Sileks Kratovo | 0:0 | ||||
| 10. Ronde | 09.10.2022 | Sileks Kratovo | - | FK Pobeda Junior | 0:3 | ||||
| 11. Ronde | 15.10.2022 | FK Bregalnica Štip | - | Sileks Kratovo | 2:3 | ||||
| 12. Ronde | 26.10.2022 | FK Rabotnički | - | Sileks Kratovo | 0:1 | ||||
| 13. Ronde | 30.10.2022 | Sileks Kratovo | - | KF Shkëndija 79 | 1:1 | |
|||
| 16. Ronde | 26.11.2022 | Sileks Kratovo | - | FC Struga | 1:2 | ||||
| 17. Ronde | 04.12.2022 | GFK Tikvesh | - | Sileks Kratovo | 0:2 | |
|||
| 20. Ronde | 26.02.2023 | Sileks Kratovo | - | KF Shkupi | 2:1 | ||||
| 22. Ronde | 08.03.2023 | Sileks Kratovo | - | FK Bregalnica Štip | 1:2 | |
|||
| 24. Ronde | 18.03.2023 | FK Pobeda Junior | - | Sileks Kratovo | 1:5 | |
|||
| 31. Ronde | 07.05.2023 | FC Struga | - | Sileks Kratovo | 3:0 | ||||
| 33. Ronde | 14.05.2023 | FK AP Brera Strumica | - | Sileks Kratovo | 2:2 | |
Noord-Macedonië