1. Round | 07/08/2022 | Akademija Pandev | - | FK Bregalnica Štip | 1:2 | ||||
4. Round | 28/08/2022 | FK Bregalnica Štip | - | Makedonija GP | 1:0 | ||||
7. Round | 11/09/2022 | FK Pobeda Junior | - | FK Bregalnica Štip | 1:0 | ||||
9. Round | 01/10/2022 | FK Bregalnica Štip | - | FK Rabotnički | 1:3 | ||||
11. Round | 15/10/2022 | FK Bregalnica Štip | - | Sileks Kratovo | 2:3 | ||||
12. Round | 25/10/2022 | FK Bregalnica Štip | - | Akademija Pandev | 1:0 | ||||
14. Round | 06/11/2022 | FK Bregalnica Štip | - | GFK Tikvesh | 2:1 | ||||
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 | ||||
19. Round | 19/02/2023 | FK Bregalnica Štip | - | FK Skopje | 0:0 | ||||
30. Round | 30/04/2023 | FK Bregalnica Štip | - | FC Struga | 0:3 |