| 3. Round | 21/08/2022 | FC Struga | - | FK Rabotnički | 2:1 |  |
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| 4. Round | 28/08/2022 | FK Rabotnički | - | GFK Tikvesh | 2:0 | |
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| 5. Round | 31/08/2022 | Makedonija GP | - | FK Rabotnički | 1:1 | ||||
| 7. Round | 11/09/2022 | KF Shkupi | - | FK Rabotnički | 5:0 |  |
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| 9. Round | 01/10/2022 | FK Bregalnica Štip | - | FK Rabotnički | 1:3 | ||||
| 12. Round | 26/10/2022 | FK Rabotnički | - | Sileks Kratovo | 0:1 | ||||
| 13. Round | 30/10/2022 | FK AP Brera Strumica | - | FK Rabotnički | 0:2 | ||||
| 14. Round | 06/11/2022 | FK Rabotnički | - | FC Struga | 1:1 | |
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| 15. Round | 12/11/2022 | GFK Tikvesh | - | FK Rabotnički | 3:0 | ||||
| 16. Round | 27/11/2022 | FK Rabotnički | - | Makedonija GP | 2:0 | ||||
| 18. Round | 11/12/2022 | FK Rabotnički | - | KF Shkupi | 2:4 | ||||
| 19. Round | 19/02/2023 | FK Pobeda Junior | - | FK Rabotnički | 0:2 | |
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| 20. Round | 26/02/2023 | FK Rabotnički | - | FK Bregalnica Štip | 0:1 | ||||
| 24. Round | 18/03/2023 | FK Rabotnički | - | FC Struga | 0:1 | ||||
| 25. Round | 02/04/2023 | Makedonija GP | - | FK Rabotnički | 2:1 | |
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| 31. Round | 07/05/2023 | FK Rabotnički | - | FK Bregalnica Štip | 5:4 | ||||
| 33. Round | 14/05/2023 | FK Rabotnički | - | KF Shkëndija 79 | 1:2 |
North Macedonia