| 1. Jornada | 10.08.2019 | FC Struga | - | FK Rabotnički | 2:1 | ||||
| 3. Jornada | 24.08.2019 | Vardar Skopje | - | FK Rabotnički | 2:0 |  |
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| 7. Jornada | 21.09.2019 | FK Borec | - | FK Rabotnički | 1:1 | ||||
| 9. Jornada | 04.10.2019 | FK Rabotnički | - | FK Renova | 1:0 | ||||
| 10. Jornada | 19.10.2019 | FK Rabotnički | - | FC Struga | 1:2 | ||||
| 11. Jornada | 23.10.2019 | KF Shkupi | - | FK Rabotnički | 2:0 | ||||
| 12. Jornada | 26.10.2019 | FK Rabotnički | - | Vardar Skopje | 0:2 | ||||
| 13. Jornada | 02.11.2019 | FK AP Brera Strumica | - | FK Rabotnički | 1:1 | |
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| 14. Jornada | 10.11.2019 | FK Rabotnički | - | KF Shkëndija 79 | 1:2 | |
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| 15. Jornada | 23.11.2019 | Makedonija GP | - | FK Rabotnički | 2:0 | ||||
| 16. Jornada | 27.11.2019 | FK Rabotnički | - | FK Borec | 2:1 | ||||
| 18. Jornada | 08.12.2019 | FK Renova | - | FK Rabotnički | 4:3 | |
Macedonia del Norte