| 8. Round | 18/09/2022 | FK Skopje | - | FK Bregalnica Štip | 0:0 | ||||
| 9. Round | 02/10/2022 | GFK Tikvesh | - | FK Skopje | 2:0 | ||||
| 12. Round | 26/10/2022 | FK Skopje | - | KF Shkëndija 79 | 0:1 | ||||
| 17. Round | 04/12/2022 | FK Pobeda Junior | - | FK Skopje | 0:0 | ||||
| 18. Round | 11/12/2022 | FK Skopje | - | FC Struga | 1:1 | ||||
| 27. Round | 15/04/2023 | FK Rabotnički | - | FK Skopje | 1:0 | ||||
| 28. Round | 23/04/2023 | FK Skopje | - | FK AP Brera Strumica | 1:1 | ||||
| 29. Round | 26/04/2023 | Makedonija GP | - | FK Skopje | 2:1 |  |
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| 32. Round | 10/05/2023 | GFK Tikvesh | - | FK Skopje | 4:0 |
Mali