| 1. Round | 06/08/2023 | FK Bregalnica Štip | - | Sileks Kratovo | 2:1 |  |
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| 2. Round | 13/08/2023 | Makedonija GP | - | FK Bregalnica Štip | 1:0 | ||||
| 3. Round | 20/08/2023 | FK Bregalnica Štip | - | KF Gostivari | 2:1 | ||||
| 4. Round | 23/08/2023 | KF Shkëndija 79 | - | FK Bregalnica Štip | 2:0 | ||||
| 5. Round | 27/08/2023 | FK Bregalnica Štip | - | FK AP Brera Strumica | 1:0 | ||||
| 6. Round | 02/09/2023 | FK Voska Sport | - | FK Bregalnica Štip | 2:0 | ||||
| 7. Round | 17/09/2023 | FK Bregalnica Štip | - | FC Struga | 1:3 | ||||
| 10. Round | 07/10/2023 | FK Bregalnica Štip | - | FK Rabotnički | 2:1 | ||||
| 19. Round | 18/02/2024 | FK Bregalnica Štip | - | GFK Tikvesh | 2:1 | ||||
| 21. Round | 03/03/2024 | FK Rabotnički | - | FK Bregalnica Štip | 2:0 | ||||
| 22. Round | 06/03/2024 | FK Bregalnica Štip | - | KF Shkupi | 0:0 |  |
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| 23. Round | 10/03/2024 | GFK Tikvesh | - | FK Bregalnica Štip | 2:1 | ||||
| 32. Round | 12/05/2024 | Makedonija GP | - | FK Bregalnica Štip | 2:1 | ||||
| 33. Round | 18/05/2024 | FK Bregalnica Štip | - | Sileks Kratovo | 1:1 |
North Macedonia