| 2. Jornada | 18.08.2018 | FK Rabotnički | - | Sileks Kratovo | 2:1 | ||||
| 6. Jornada | 23.09.2018 | Sileks Kratovo | - | KF Shkëndija 79 | 1:2 | ||||
| 8. Jornada | 29.09.2018 | Sileks Kratovo | - | Makedonija GP | 1:1 | ||||
| 9. Jornada | 06.10.2018 | FK Belasica | - | Sileks Kratovo | 1:1 | ||||
| 11. Jornada | 28.10.2018 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
| 12. Jornada | 31.10.2018 | FK Renova | - | Sileks Kratovo | 1:1 | ||||
| 13. Jornada | 04.11.2018 | FK Pobeda | - | Sileks Kratovo | 2:0 |
Macedonia del Norte