| 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 |  |
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| 4. Ronde | 31.08.2019 | FK Rabotnički | - | FK AP Brera Strumica | 1:2 | ||||
| 6. Ronde | 18.09.2019 | FK Rabotnički | - | Makedonija GP | 1:0 | ||||
| 7. Ronde | 21.09.2019 | FK Borec | - | FK Rabotnički | 1:1 | ||||
| 8. Ronde | 29.09.2019 | Sileks Kratovo | - | FK Rabotnički | 1:0 | ||||
| 10. Ronde | 19.10.2019 | FK Rabotnički | - | FC Struga | 1:2 | |
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| 13. Ronde | 02.11.2019 | FK AP Brera Strumica | - | FK Rabotnički | 1:1 | ||||
| 14. Ronde | 10.11.2019 | FK Rabotnički | - | KF Shkëndija 79 | 1:2 | ||||
| 16. Ronde | 27.11.2019 | FK Rabotnički | - | FK Borec | 2:1 | ||||
| 17. Ronde | 01.12.2019 | FK Rabotnički | - | Sileks Kratovo | 1:1 | ||||
| 18. Ronde | 08.12.2019 | FK Renova | - | FK Rabotnički | 4:3 | |
Brazilië
Portugal