Bregalnica Stip 3-6 Akademija Pandev *
| 03.10.2018 | Akademija Pandev | 0-1 | Bregalnica Stip | |
| 19.09.2018 | Bregalnica Stip | 2-6 | Akademija Pandev | |
Gostivari 2-6 Pobeda Prilep *
| 03.10.2018 | Pobeda Prilep | 4-1 | Gostivari | |
| 19.09.2018 | Gostivari | 1-2 | Pobeda Prilep | |
*Shkendija'79 7-0 Kit-Go Pehčevo
| 03.10.2018 | Kit-Go Pehčevo | 0-5 | Shkendija'79 | |
| 19.09.2018 | Shkendija'79 | 2-0 | Kit-Go Pehčevo | |
Vardar Skopje 2-3 Makedonija GP *
| 03.10.2018 | Makedonija GP | 2-1 | Vardar Skopje | |
| 19.09.2018 | Vardar Skopje | 1-1 | Makedonija GP | |
Pelister Bitola 1-5 Belasica Strumica *
| 03.10.2018 | Belasica Strumica | 3-1 | Pelister Bitola | |
| 19.09.2018 | Pelister Bitola | 0-2 | Belasica Strumica | |
Tikves Kavadarci 1-2 Rabotnicki Skopje *
| 03.10.2018 | Rabotnicki Skopje | 1-1 | Tikves Kavadarci | |
| 19.09.2018 | Tikves Kavadarci | 0-1 | Rabotnicki Skopje | |
FK Skopje 1-4 Sileks Kratovo *
| 03.10.2018 | Sileks Kratovo | 2-1 | FK Skopje | |
| 19.09.2018 | FK Skopje | 0-2 | Sileks Kratovo | |