| 1. Jornada | 10.08.2019 | FC Struga | - | FK Rabotnički | 2:1 | ||||
| 2. Jornada | 17.08.2019 | FK Rabotnički | - | KF Shkupi | 2:0 | ||||
| 3. Jornada | 24.08.2019 | Vardar Skopje | - | FK Rabotnički | 2:0 |  |
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| 4. Jornada | 31.08.2019 | FK Rabotnički | - | FK AP Brera Strumica | 1:2 | ||||
| 6. Jornada | 18.09.2019 | FK Rabotnički | - | Makedonija GP | 1:0 | ||||
| 7. Jornada | 21.09.2019 | FK Borec | - | FK Rabotnički | 1:1 | ||||
| 8. Jornada | 29.09.2019 | Sileks Kratovo | - | FK Rabotnički | 1:0 | ||||
| 10. Jornada | 19.10.2019 | FK Rabotnički | - | FC Struga | 1:2 | |
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| 13. Jornada | 02.11.2019 | FK AP Brera Strumica | - | FK Rabotnički | 1:1 | ||||
| 14. Jornada | 10.11.2019 | FK Rabotnički | - | KF Shkëndija 79 | 1:2 | ||||
| 16. Jornada | 27.11.2019 | FK Rabotnički | - | FK Borec | 2:1 | ||||
| 17. Jornada | 01.12.2019 | FK Rabotnički | - | Sileks Kratovo | 1:1 | ||||
| 18. Jornada | 08.12.2019 | FK Renova | - | FK Rabotnički | 4:3 | |
Brasil
Portugal