| 1. Round | 06/08/2022 | FC Struga | - | FK Pobeda Junior | 3:0 | ||||
| 2. Round | 14/08/2022 | FK Pobeda Junior | - | GFK Tikvesh | 0:1 | ||||
| 10. Round | 09/10/2022 | Sileks Kratovo | - | FK Pobeda Junior | 0:3 |  |
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| 11. Round | 15/10/2022 | FK Pobeda Junior | - | FK AP Brera Strumica | 1:1 | ||||
| 12. Round | 26/10/2022 | FK Pobeda Junior | - | FC Struga | 2:0 | ||||
| 13. Round | 30/10/2022 | GFK Tikvesh | - | FK Pobeda Junior | 1:0 | ||||
| 14. Round | 06/11/2022 | FK Pobeda Junior | - | Makedonija GP | 1:3 |  |
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| 16. Round | 27/11/2022 | FK Pobeda Junior | - | KF Shkupi | 0:6 | ||||
| 17. Round | 04/12/2022 | FK Pobeda Junior | - | FK Skopje | 0:0 | ||||
| 18. Round | 11/12/2022 | FK Bregalnica Štip | - | FK Pobeda Junior | 2:2 | |
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| 19. Round | 19/02/2023 | FK Pobeda Junior | - | FK Rabotnički | 0:2 | ||||
| 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 | ||||
| 26. Round | 09/04/2023 | FK Pobeda Junior | - | KF Shkupi | 0:6 | ||||
| 28. Round | 23/04/2023 | FK Pobeda Junior | - | FK Rabotnički | 0:1 | |
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| 29. Round | 26/04/2023 | FK AP Brera Strumica | - | FK Pobeda Junior | 2:0 | ||||
| 30. Round | 30/04/2023 | FK Pobeda Junior | - | FK Skopje | 0:4 | |
North Macedonia