| 4. Jornada | 07.09.2018 | Helmond Sport | - | FC Den Bosch | 0:2 | ||||
| 5. Jornada | 17.09.2018 | Jong Ajax | - | Helmond Sport | 2:0 | ||||
| 7. Jornada | 28.09.2018 | Helmond Sport | - | FC Volendam | 2:2 | ||||
| 8. Jornada | 05.10.2018 | AZ Alkmaar (J) | - | Helmond Sport | 2:2 | ||||
| 9. Jornada | 12.10.2018 | Helmond Sport | - | Telstar | 1:2 | ||||
| 10. Jornada | 19.10.2018 | SC Cambuur | - | Helmond Sport | 3:1 | ||||
| 13. Jornada | 09.11.2018 | Roda JC Kerkrade | - | Helmond Sport | 3:0 |  |
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| 14. Jornada | 17.11.2018 | Helmond Sport | - | RKC Waalwijk | 0:2 | ||||
| 17. Jornada | 07.12.2018 | Go Ahead Eagles | - | Helmond Sport | 1:0 | ||||
| 18. Jornada | 14.12.2018 | TOP Oss | - | Helmond Sport | 1:1 | ||||
| 19. Jornada | 21.12.2018 | Helmond Sport | - | FC Utrecht (J) | 2:0 | ||||
| 20. Jornada | 13.01.2019 | Telstar | - | Helmond Sport | 1:1 | ||||
| 21. Jornada | 18.01.2019 | Helmond Sport | - | SC Cambuur | 0:1 | ||||
| 22. Jornada | 25.01.2019 | MVV | - | Helmond Sport | 3:0 | ||||
| 24. Jornada | 08.02.2019 | Helmond Sport | - | FC Dordrecht | 1:2 | ||||
| 25. Jornada | 15.02.2019 | FC Volendam | - | Helmond Sport | 1:0 | ||||
| 27. Jornada | 01.03.2019 | Helmond Sport | - | Jong PSV | 0:2 | ||||
| 29. Jornada | 15.03.2019 | Helmond Sport | - | Go Ahead Eagles | 1:1 |
Países Bajos