3. Round | 20/08/2023 | KF Shkupi | - | Sileks Kratovo | 1:1 | ||||
9. Round | 01/10/2023 | Sileks Kratovo | - | FK Voska Sport | 4:2 | ||||
10. Round | 08/10/2023 | FC Struga | - | Sileks Kratovo | 2:0 | ||||
22. Round | 06/03/2024 | GFK Tikvesh | - | Sileks Kratovo | 1:0 | ||||
25. Round | 30/03/2024 | GFK Tikvesh | - | Sileks Kratovo | 1:1 | ||||
33. Round | 18/05/2024 | FK Bregalnica Štip | - | Sileks Kratovo | 1:1 |