1. Round | 09/08/2019 | Helmond Sport | - | FC Volendam | 1:1 | ||||
2. Round | 16/08/2019 | NAC Breda | - | Helmond Sport | 5:1 | ||||
3. Round | 23/08/2019 | Helmond Sport | - | Almere City FC | 1:1 | ||||
4. Round | 30/08/2019 | SBV Excelsior | - | Helmond Sport | 3:1 | ||||
7. Round | 21/09/2019 | Helmond Sport | - | TOP Oss | 0:2 | ||||
11. Round | 18/10/2019 | FC Dordrecht | - | Helmond Sport | 1:2 | ||||
12. Round | 25/10/2019 | Helmond Sport | - | Telstar | 1:4 | ||||
13. Round | 01/11/2019 | FC Den Bosch | - | Helmond Sport | 1:1 | ||||
14. Round | 08/11/2019 | Helmond Sport | - | De Graafschap | 1:2 | ||||
16. Round | 22/11/2019 | Helmond Sport | - | NEC Nijmegen | 1:2 | ||||
19. Round | 13/12/2019 | Helmond Sport | - | Go Ahead Eagles | 1:2 |