1. Round | 06/08/2023 | FK Bregalnica Štip | - | Sileks Kratovo | 2:1 | ||||
2. Round | 13/08/2023 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
3. Round | 20/08/2023 | KF Shkupi | - | Sileks Kratovo | 1:1 | ||||
4. Round | 23/08/2023 | Vardar Skopje | - | Sileks Kratovo | 2:2 | ||||
5. Round | 27/08/2023 | Sileks Kratovo | - | Makedonija GP | 2:2 | ||||
6. Round | 02/09/2023 | KF Gostivari | - | Sileks Kratovo | 1:2 | ||||
7. Round | 17/09/2023 | Sileks Kratovo | - | KF Shkëndija 79 | 2:1 | ||||
8. Round | 24/09/2023 | Akademija Pandev | - | 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 | ||||
12. Round | 28/10/2023 | Sileks Kratovo | - | FK Bregalnica Štip | 0:0 | ||||
13. Round | 04/11/2023 | FK Rabotnički | - | Sileks Kratovo | 1:0 | ||||
17. Round | 03/12/2023 | Sileks Kratovo | - | KF Gostivari | 1:1 | ||||
15. Round | 06/12/2023 | Sileks Kratovo | - | Vardar Skopje | 3:2 | ||||
18. Round | 10/12/2023 | KF Shkëndija 79 | - | Sileks Kratovo | 3:1 |