3. Round | 31/08/2018 | Jong PSV | - | Helmond Sport | 1:1 | ||||
4. Round | 07/09/2018 | Helmond Sport | - | FC Den Bosch | 0:2 | ||||
6. Round | 21/09/2018 | Helmond Sport | - | NEC Nijmegen | 2:3 | ||||
7. Round | 28/09/2018 | Helmond Sport | - | FC Volendam | 2:2 | ||||
8. Round | 05/10/2018 | AZ Alkmaar (J) | - | Helmond Sport | 2:2 | ||||
9. Round | 12/10/2018 | Helmond Sport | - | Telstar | 1:2 | ||||
13. Round | 09/11/2018 | Roda JC Kerkrade | - | Helmond Sport | 3:0 | ||||
14. Round | 17/11/2018 | Helmond Sport | - | RKC Waalwijk | 0:2 | ||||
15. Round | 23/11/2018 | FC Eindhoven | - | Helmond Sport | 2:1 | ||||
16. Round | 30/11/2018 | Helmond Sport | - | Sparta Rotterdam | 3:0 | ||||
29. Round | 15/03/2019 | Helmond Sport | - | Go Ahead Eagles | 1:1 | ||||
31. Round | 29/03/2019 | Helmond Sport | - | Roda JC Kerkrade | 4:0 | ||||
32. Round | 01/04/2019 | Almere City FC | - | Helmond Sport | 3:0 | ||||
33. Round | 05/04/2019 | Helmond Sport | - | Jong Ajax | 1:3 | ||||
34. Round | 12/04/2019 | NEC Nijmegen | - | Helmond Sport | 3:2 |