| 1. Round | 07/08/2022 | Sileks Kratovo | - | FK Rabotnički | 2:0 |  |
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| 4. Round | 28/08/2022 | FK Rabotnički | - | GFK Tikvesh | 2:0 | ||||
| 5. Round | 31/08/2022 | Makedonija GP | - | FK Rabotnički | 1:1 | ||||
| 7. Round | 11/09/2022 | KF Shkupi | - | FK Rabotnički | 5:0 | ||||
| 8. Round | 17/09/2022 | FK Rabotnički | - | FK Pobeda Junior | 1:0 | ||||
| 10. Round | 09/10/2022 | FK Skopje | - | FK Rabotnički | 0:0 | |
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| 11. Round | 15/10/2022 | FK Rabotnički | - | KF Shkëndija 79 | 2:4 | ||||
| 12. Round | 26/10/2022 | FK Rabotnički | - | Sileks Kratovo | 0:1 | ||||
| 15. Round | 12/11/2022 | GFK Tikvesh | - | FK Rabotnički | 3:0 | ||||
| 18. Round | 11/12/2022 | FK Rabotnički | - | KF Shkupi | 2:4 |
Germany