| 2. Round | 16/08/2019 | NAC Breda | - | Helmond Sport | 5:1 | ||||
| 15. Round | 25/11/2019 | Jong Ajax | - | Helmond Sport | 1:1 | ||||
| 22. Round | 17/01/2020 | FC Eindhoven | - | Helmond Sport | 2:0 | ||||
| 26. Round | 14/02/2020 | NEC Nijmegen | - | Helmond Sport | 2:0 | ||||
| 27. Round | 21/02/2020 | Helmond Sport | - | Jong Ajax | 0:2 | ||||
| 29. Round | 06/03/2020 | Helmond Sport | - | FC Dordrecht | 1:1 |
Netherlands