| 4. Round | 24/08/2009 | Helmond Sport | - | SBV Excelsior | 3:1 | ||||
| 9. Round | 25/09/2009 | FC Emmen | - | Helmond Sport | 1:3 | ||||
| 13. Round | 23/10/2009 | Helmond Sport | - | AGOVV | 4:4 | ||||
| 14. Round | 30/10/2009 | FC Zwolle | - | Helmond Sport | 3:1 | ||||
| 15. Round | 06/11/2009 | Helmond Sport | - | FC Oss | 3:1 |  |
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| 19. Round | 30/11/2009 | Go Ahead Eagles | - | Helmond Sport | 3:2 | ||||
| 20. Round | 04/12/2009 | Helmond Sport | - | MVV | 2:4 | ||||
| 30. Round | 05/03/2010 | FC Den Bosch | - | Helmond Sport | 2:1 | ||||
| 32. Round | 12/03/2010 | FC Eindhoven | - | Helmond Sport | 3:2 | |
Netherlands