*Akademija Pandev 7-1 Osogovo Kocani
| 30.10.2019 | Osogovo Kocani | 1-4 | Akademija Pandev | |
| 25.09.2019 | Akademija Pandev | 3-0 | Osogovo Kocani | |
Borec Veles 0-1 FC Struga *
| 30.10.2019 | FC Struga | 1-0 | Borec Veles | |
| 25.09.2019 | Borec Veles | 0-0 | FC Struga | |
*FK Labunishta 5-2 Ohrid Lihnidos
| 30.10.2019 | Ohrid Lihnidos | 2-3 | FK Labunishta | |
| 25.09.2019 | FK Labunishta | 2-0 | Ohrid Lihnidos | |
*Bregalnica Stip 1-0 Makedonija GP
| 30.10.2019 | Makedonija GP | 0-0 | Bregalnica Stip | |
| 25.09.2019 | Bregalnica Stip | 1-0 | Makedonija GP | |
Pelister Bitola 1-5 Rabotnicki Skopje *
| 30.10.2019 | Rabotnicki Skopje | 4-0 | Pelister Bitola | |
| 25.09.2019 | Pelister Bitola | 1-1 | Rabotnicki Skopje | |
Tikves Kavadarci 1-3 Renova *
| 31.10.2019 | Renova | 1-1 | Tikves Kavadarci | |
| 25.09.2019 | Tikves Kavadarci | 0-2 | Renova | |
*Shkupi 1-1 Sileks Kratovo
| 30.10.2019 | Sileks Kratovo | 1-1 | Shkupi | |
| 25.09.2019 | Shkupi | 0-0 | Sileks Kratovo | |
Vardar Skopje 2-3 Shkendija'79 *
| 30.10.2019 | Shkendija'79 | 1-0 | Vardar Skopje | |
| 25.09.2019 | Vardar Skopje | 2-2 | Shkendija'79 | |