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| U | GFK Tikvesh | - | FK Rabotnički | 0:1 | ||
| R | FK Rabotnički | - | GFK Tikvesh | 1:1 (0:0) | ||
| U: 19.09.2018 15:30 | R: 03.10.2018 15:00 | Winnaars: FK Rabotnički | ||||
| U | KF Gostivari | - | FK Pobeda | 1:2 | ||
| R | FK Pobeda | - | KF Gostivari | 4:1 (3:1) | ||
| U: 19.09.2018 15:30 | R: 03.10.2018 15:00 | Winnaars: FK Pobeda | ||||
| U | Vardar Skopje | - | Makedonija GP | 1:1 | ||
| R | Makedonija GP | - | Vardar Skopje | 2:1 (1:1) | ||
| U: 19.09.2018 15:30 | R: 03.10.2018 15:00 | Winnaars: Makedonija GP | ||||
| U | FK Skopje | - | Sileks Kratovo | 0:2 | ||
| R | Sileks Kratovo | - | FK Skopje | 2:1 (0:1) | ||
| U: 19.09.2018 15:30 | R: 03.10.2018 15:00 | Winnaars: Sileks Kratovo | ||||
| U | KF Shkëndija 79 | - | FK Kit-Go Pehčevo | 2:0 | ||
| R | FK Kit-Go Pehčevo | - | KF Shkëndija 79 | 0:5 (0:3) | ||
| U: 19.09.2018 15:30 | R: 03.10.2018 15:00 | Winnaars: KF Shkëndija 79 | ||||
| U | FK Bregalnica Štip | - | Akademija Pandev | 2:6 | ||
| R | Akademija Pandev | - | FK Bregalnica Štip | 0:1 (0:1) | ||
| U: 19.09.2018 15:30 | R: 03.10.2018 15:00 | Winnaars: Akademija Pandev | ||||
| U | FK Pelister | - | FK Belasica | 0:2 | ||
| R | FK Belasica | - | FK Pelister | 3:1 | ||
| U: 19.09.2018 15:30 | R: 03.10.2018 15:00 | Winnaars: FK Belasica | ||||
