| 4. Round | 31/08/2019 | FK Rabotnički | - | FK AP Brera Strumica | 1:2 | ||||
| 7. Round | 21/09/2019 | FK Borec | - | FK Rabotnički | 1:1 |  |
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| 12. Round | 26/10/2019 | FK Rabotnički | - | Vardar Skopje | 0:2 | ||||
| 14. Round | 10/11/2019 | FK Rabotnički | - | KF Shkëndija 79 | 1:2 |  |
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| 15. Round | 23/11/2019 | Makedonija GP | - | FK Rabotnički | 2:0 | ||||
| 16. Round | 27/11/2019 | FK Rabotnički | - | FK Borec | 2:1 | ||||
| 18. Round | 08/12/2019 | FK Renova | - | FK Rabotnički | 4:3 |
Colombia
North Macedonia