1. Round | 06/08/2023 | FK Bregalnica Štip | - | Sileks Kratovo | 2:1 | ||||
2. Round | 13/08/2023 | Makedonija GP | - | FK Bregalnica Štip | 1:0 | ||||
3. Round | 20/08/2023 | FK Bregalnica Štip | - | KF Gostivari | 2:1 | ||||
5. Round | 27/08/2023 | FK Bregalnica Štip | - | Akademija Pandev | 1:0 | ||||
6. Round | 02/09/2023 | FK Voska Sport | - | FK Bregalnica Štip | 2:0 |