Akademija Pandev 1-4 Shkupi *
| 12.10.2016 | Shkupi | 3-1 | Akademija Pandev | |
| 21.09.2016 | Akademija Pandev | 0-1 | Shkupi | |
*Bregalnica Stip 6-1 Teteks Tetovo
| 12.10.2016 | Teteks Tetovo | 1-2 | Bregalnica Stip | |
| 21.09.2016 | Bregalnica Stip | 4-0 | Teteks Tetovo | |
*Sileks Kratovo 5-4 FK Turnovo
| 12.10.2016 | FK Turnovo | 3-3 | Sileks Kratovo | |
| 21.09.2016 | Sileks Kratovo | 2-1 | FK Turnovo | |
Novaci 1-7 Pobeda Prilep *
| 12.10.2016 | Pobeda Prilep | 5-0 | Novaci | |
| 21.09.2016 | Novaci | 1-2 | Pobeda Prilep | |
*Pelister Bitola 3-3 Renova
| 19.10.2016 | Renova | 3-1 | Pelister Bitola | |
| 21.09.2016 | Pelister Bitola | 2-0 | Renova | |
Rabotnicki Skopje 0-2 Shkendija'79 *
| 19.10.2016 | Shkendija'79 | 0-0 | Rabotnicki Skopje | |
| 21.09.2016 | Rabotnicki Skopje | 0-2 | Shkendija'79 | |
Vlazrimi Kicevo 1-5 Vardar Skopje *
| 19.10.2016 | Vardar Skopje | 2-0 | Vlazrimi Kicevo | |
| 21.09.2016 | Vlazrimi Kicevo | 1-3 | Vardar Skopje | |