| 1. Jornada | 10.08.2019 | FC Struga | - | FK Rabotnički | 2:1 | ||||
| 3. Jornada | 24.08.2019 | Vardar Skopje | - | FK Rabotnički | 2:0 | ||||
| 4. Jornada | 31.08.2019 | FK Rabotnički | - | FK AP Brera Strumica | 1:2 | ||||
| 7. Jornada | 21.09.2019 | FK Borec | - | FK Rabotnički | 1:1 | ||||
| 11. Jornada | 23.10.2019 | KF Shkupi | - | FK Rabotnički | 2:0 | ||||
| 13. Jornada | 02.11.2019 | FK AP Brera Strumica | - | FK Rabotnički | 1:1 |
Serbia