1. Ronde | 10.08.2019 | FC Struga | - | FK Rabotnički | 2:1 | ||||
2. Ronde | 17.08.2019 | FK Rabotnički | - | KF Shkupi | 2:0 | ||||
3. Ronde | 24.08.2019 | Vardar Skopje | - | FK Rabotnički | 2:0 | ||||
4. Ronde | 31.08.2019 | FK Rabotnički | - | Akademija Pandev | 1:2 | ||||
5. Ronde | 14.09.2019 | KF Shkëndija 79 | - | FK Rabotnički | 3:0 |