| 4. Ronde | 31.08.2019 | FK Rabotnički | - | FK AP Brera Strumica | 1:2 | ||||
| 7. Ronde | 21.09.2019 | FK Borec | - | FK Rabotnički | 1:1 |  |
|||
| 12. Ronde | 26.10.2019 | FK Rabotnički | - | Vardar Skopje | 0:2 | ||||
| 14. Ronde | 10.11.2019 | FK Rabotnički | - | KF Shkëndija 79 | 1:2 |  |
|||
| 15. Ronde | 23.11.2019 | Makedonija GP | - | FK Rabotnički | 2:0 | ||||
| 16. Ronde | 27.11.2019 | FK Rabotnički | - | FK Borec | 2:1 | ||||
| 18. Ronde | 08.12.2019 | FK Renova | - | FK Rabotnički | 4:3 |
Colombia
Noord-Macedonië