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| 1st(1st leg) | KF Shkëndija 79 | - | FK Pobeda | 0:1 (0:1) | ||
| 2nd (2nd leg) | FK Pobeda | - | KF Shkëndija 79 | 2:0 (1:0) | ||
| 1st(1st leg): 07/11/2018 12:00 | 2nd (2nd leg): 05/12/2018 12:00 | Winner: FK Pobeda | ||||
| 1st(1st leg) | Sileks Kratovo | - | FK Belasica | 0:2 (0:0) | ||
| 2nd (2nd leg) | FK Belasica | - | Sileks Kratovo | 2:0 (0:0) | ||
| 1st(1st leg): 07/11/2018 12:00 | 2nd (2nd leg): 05/12/2018 12:00 | Winner: FK Belasica | ||||
| 1st(1st leg) | Akademija Pandev | - | KF Korabi | 3:1 (2:1) | ||
| 2nd (2nd leg) | KF Korabi | - | Akademija Pandev | 1:6 (1:2) | ||
| 1st(1st leg): 07/11/2018 12:00 | 2nd (2nd leg): 05/12/2018 12:00 | Winner: Akademija Pandev | ||||
| 1st(1st leg) | Makedonija GP | - | FK Rabotnički | 1:0 (0:0) | ||
| 2nd (2nd leg) | FK Rabotnički | - | Makedonija GP | 0:1 (0:0) | ||
| 1st(1st leg): 07/11/2018 12:00 | 2nd (2nd leg): 05/12/2018 12:00 | Winner: Makedonija GP | ||||
