| 1. Round | 06/08/2022 | FC Struga | - | FK Pobeda Junior | 3:0 | ||||
| 5. Round | 31/08/2022 | KF Shkupi | - | FK Pobeda Junior | 1:1 | ||||
| 6. Round | 04/09/2022 | FK Skopje | - | FK Pobeda Junior | 1:0 |  |
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| 7. Round | 11/09/2022 | FK Pobeda Junior | - | FK Bregalnica Štip | 1:0 |  |
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| 8. Round | 17/09/2022 | FK Rabotnički | - | FK Pobeda Junior | 1:0 | |
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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 | ||||
| 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 | ||||
| 25. Round | 02/04/2023 | KF Shkëndija 79 | - | FK Pobeda Junior | 2:0 | ||||
| 26. Round | 09/04/2023 | FK Pobeda Junior | - | KF Shkupi | 0:6 |
North Macedonia