| 4. Ronde | 28.08.2022 | FK Skopje | - | KF Shkupi | 0:2 | ||||
| 6. Ronde | 04.09.2022 | FK Bregalnica Štip | - | KF Shkupi | 2:0 | ||||
| 1. Ronde | 07.09.2022 | GFK Tikvesh | - | KF Shkupi | 3:1 | ||||
| 10. Ronde | 09.10.2022 | FK AP Brera Strumica | - | KF Shkupi | 0:1 | ||||
| 15. Ronde | 12.11.2022 | KF Shkupi | - | FK Skopje | 3:1 | ||||
| 18. Ronde | 11.12.2022 | FK Rabotnički | - | KF Shkupi | 2:4 | ||||
| 26. Ronde | 09.04.2023 | FK Pobeda Junior | - | KF Shkupi | 0:6 | ||||
| 30. Ronde | 30.04.2023 | Sileks Kratovo | - | KF Shkupi | 0:2 | ||||
| 33. Ronde | 14.05.2023 | FC Struga | - | KF Shkupi | 2:1 |
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