| 19. Ronde | 17.02.2019 | FK Rabotnički | - | FK Renova | 1:1 | ||||
| 20. Ronde | 24.02.2019 | FK Rabotnički | - | Sileks Kratovo | 1:1 | ||||
| 21. Ronde | 03.03.2019 | FK Pobeda | - | FK Rabotnički | 0:1 | ||||
| 22. Ronde | 10.03.2019 | FK Rabotnički | - | FK AP Brera Strumica | 1:2 |  |
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| 23. Ronde | 16.03.2019 | KF Shkëndija 79 | - | FK Rabotnički | 1:0 | ||||
| 24. Ronde | 28.03.2019 | FK Rabotnički | - | Vardar Skopje | 0:2 | ||||
| 25. Ronde | 31.03.2019 | Makedonija GP | - | FK Rabotnički | 1:1 | ||||
| 26. Ronde | 03.04.2019 | FK Rabotnički | - | FK Belasica | 1:1 | ||||
| 27. Ronde | 07.04.2019 | KF Shkupi | - | FK Rabotnički | 1:2 | |
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| 28. Ronde | 14.04.2019 | FK Renova | - | FK Rabotnički | 1:2 |  |
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| 29. Ronde | 20.04.2019 | Sileks Kratovo | - | FK Rabotnički | 1:0 | |
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| 30. Ronde | 24.04.2019 | FK Rabotnički | - | FK Pobeda | 1:2 | |
|
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| 31. Ronde | 27.04.2019 | FK AP Brera Strumica | - | FK Rabotnički | 3:1 | |
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| 32. Ronde | 04.05.2019 | FK Rabotnički | - | KF Shkëndija 79 | 0:1 | ||||
| 33. Ronde | 08.05.2019 | Vardar Skopje | - | FK Rabotnički | 1:1 |  |
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| 35. Ronde | 19.05.2019 | FK Belasica | - | FK Rabotnički | 0:1 | ||||
| 36. Ronde | 26.05.2019 | FK Rabotnički | - | KF Shkupi | 1:2 |
Bulgarije