| 19. Round | 17/02/2019 | FK Rabotnički | - | FK Renova | 1:1 | ||||
| 20. Round | 24/02/2019 | FK Rabotnički | - | Sileks Kratovo | 1:1 |  |
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| 21. Round | 03/03/2019 | FK Pobeda | - | FK Rabotnički | 0:1 | ||||
| 22. Round | 10/03/2019 | FK Rabotnički | - | FK AP Brera Strumica | 1:2 | ||||
| 23. Round | 16/03/2019 | KF Shkëndija 79 | - | FK Rabotnički | 1:0 | |
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| 24. Round | 28/03/2019 | FK Rabotnički | - | Vardar Skopje | 0:2 | ||||
| 25. Round | 31/03/2019 | Makedonija GP | - | FK Rabotnički | 1:1 | ||||
| 26. Round | 03/04/2019 | FK Rabotnički | - | FK Belasica | 1:1 | ||||
| 28. Round | 14/04/2019 | FK Renova | - | FK Rabotnički | 1:2 | ||||
| 29. Round | 20/04/2019 | Sileks Kratovo | - | FK Rabotnički | 1:0 | ||||
| 30. Round | 24/04/2019 | FK Rabotnički | - | FK Pobeda | 1:2 | ||||
| 31. Round | 27/04/2019 | FK AP Brera Strumica | - | FK Rabotnički | 3:1 | |
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| 33. Round | 08/05/2019 | Vardar Skopje | - | FK Rabotnički | 1:1 | ||||
| 34. Round | 12/05/2019 | FK Rabotnički | - | Makedonija GP | 2:0 | ||||
| 35. Round | 19/05/2019 | FK Belasica | - | FK Rabotnički | 0:1 |
North Macedonia