1. Round | 07/08/2022 | Akademija Pandev | - | 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 | ||||
11. Round | 15/10/2022 | FK Bregalnica Štip | - | Sileks Kratovo | 2:3 | ||||
14. Round | 06/11/2022 | FK Bregalnica Štip | - | GFK Tikvesh | 2:1 | ||||
15. Round | 13/11/2022 | Makedonija GP | - | FK Bregalnica Štip | 0:0 | ||||
18. Round | 11/12/2022 | FK Bregalnica Štip | - | FK Pobeda Junior | 2:2 |