2. Round | 18/08/2018 | FK Rabotnički | - | Sileks Kratovo | 2:1 | ||||
6. Round | 23/09/2018 | Sileks Kratovo | - | KF Shkëndija 79 | 1:2 | ||||
8. Round | 29/09/2018 | Sileks Kratovo | - | Makedonija GP | 1:1 | ||||
9. Round | 06/10/2018 | FK Belasica | - | Sileks Kratovo | 1:1 | ||||
11. Round | 28/10/2018 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
12. Round | 31/10/2018 | FK Renova | - | Sileks Kratovo | 1:1 | ||||
13. Round | 04/11/2018 | FK Pobeda | - | Sileks Kratovo | 2:0 |