| 1. Round | 07/08/2022 | FK AP Brera Strumica | - | FK Bregalnica Štip | 1:2 | ||||
| 2. Round | 14/08/2022 | FK Bregalnica Štip | - | FC Struga | 0:1 | ||||
| 3. Round | 21/08/2022 | GFK Tikvesh | - | FK Bregalnica Štip | 1:1 | ||||
| 4. Round | 28/08/2022 | FK Bregalnica Štip | - | Makedonija GP | 1:0 | ||||
| 6. Round | 04/09/2022 | FK Bregalnica Štip | - | KF Shkupi | 2:0 | ||||
| 7. Round | 11/09/2022 | FK Pobeda Junior | - | FK Bregalnica Štip | 1:0 | ||||
| 8. Round | 18/09/2022 | FK Skopje | - | FK Bregalnica Štip | 0:0 | ||||
| 9. Round | 01/10/2022 | FK Bregalnica Štip | - | FK Rabotnički | 1:3 | ||||
| 10. Round | 09/10/2022 | KF Shkëndija 79 | - | FK Bregalnica Štip | 0:0 |  |
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| 12. Round | 25/10/2022 | FK Bregalnica Štip | - | FK AP Brera Strumica | 1:0 |  |
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| 13. Round | 30/10/2022 | FC Struga | - | FK Bregalnica Štip | 2:2 | |
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| 14. Round | 06/11/2022 | FK Bregalnica Štip | - | GFK Tikvesh | 2:1 | |
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| 15. Round | 13/11/2022 | Makedonija GP | - | FK Bregalnica Štip | 0:0 | |
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| 17. Round | 04/12/2022 | KF Shkupi | - | FK Bregalnica Štip | 3:1 | ||||
| 18. Round | 11/12/2022 | FK Bregalnica Štip | - | FK Pobeda Junior | 2:2 | |
North Macedonia