| 3. Round | 20/08/2022 | Makedonija GP | - | FK Pobeda Junior | 4:1 | ||||
| 7. Round | 11/09/2022 | FK Pobeda Junior | - | FK Bregalnica Štip | 1:0 | ||||
| 10. Round | 09/10/2022 | Sileks Kratovo | - | FK Pobeda Junior | 0:3 | ||||
| 13. Round | 30/10/2022 | GFK Tikvesh | - | FK Pobeda Junior | 1:0 | ||||
| 18. Round | 11/12/2022 | FK Bregalnica Štip | - | FK Pobeda Junior | 2:2 | ||||
| 19. Round | 19/02/2023 | FK Pobeda Junior | - | FK Rabotnički | 0:2 | ||||
| 20. Round | 26/02/2023 | KF Shkëndija 79 | - | FK Pobeda Junior | 1:0 | ||||
| 21. Round | 05/03/2023 | FK Pobeda Junior | - | Sileks Kratovo | 1:4 | ||||
| 22. Round | 08/03/2023 | FK AP Brera Strumica | - | FK Pobeda Junior | 3:0 | ||||
| 23. Round | 12/03/2023 | FK Bregalnica Štip | - | FK Pobeda Junior | 4:0 | ||||
| 24. Round | 18/03/2023 | FK Pobeda Junior | - | Sileks Kratovo | 1:5 | ||||
| 25. Round | 02/04/2023 | KF Shkëndija 79 | - | FK Pobeda Junior | 2:0 |  |
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| 26. Round | 09/04/2023 | FK Pobeda Junior | - | KF Shkupi | 0:6 | ||||
| 27. Round | 15/04/2023 | FC Struga | - | FK Pobeda Junior | 6:2 | ||||
| 28. Round | 23/04/2023 | FK Pobeda Junior | - | FK Rabotnički | 0:1 | ||||
| 30. Round | 30/04/2023 | FK Pobeda Junior | - | FK Skopje | 0:4 | |
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| 33. Round | 14/05/2023 | FK Pobeda Junior | - | GFK Tikvesh | 1:4 |
North Macedonia