| 1. Round | 07/08/2009 | Fortuna Sittard | - | Helmond Sport | 0:4 | ||||
| 2. Round | 14/08/2009 | Helmond Sport | - | SC Cambuur | 2:4 |  |
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| 3. Round | 21/08/2009 | Telstar | - | Helmond Sport | 1:4 | ||||
| 7. Round | 10/09/2009 | HFC Haarlem | - | Helmond Sport | annull. | ||||
| 9. Round | 25/09/2009 | FC Emmen | - | Helmond Sport | 1:3 | |
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| 10. Round | 02/10/2009 | Helmond Sport | - | FC Omniworld | 2:1 | ||||
| 14. Round | 30/10/2009 | FC Zwolle | - | Helmond Sport | 3:1 | ||||
| 15. Round | 06/11/2009 | Helmond Sport | - | FC Oss | 3:1 | ||||
| 16. Round | 13/11/2009 | RBC Roosendaal | - | Helmond Sport | 2:1 | |
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| 20. Round | 04/12/2009 | Helmond Sport | - | MVV | 2:4 | ||||
| 22. Round | 18/01/2010 | Helmond Sport | - | BV Veendam | 4:1 | ||||
| 24. Round | 22/01/2010 | De Graafschap | - | Helmond Sport | 4:0 | ||||
| 25. Round | 29/01/2010 | FC Omniworld | - | Helmond Sport | 1:0 | ||||
| 26. Round | 05/02/2010 | Helmond Sport | - | FC Zwolle | 2:0 | |
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| 27. Round | 22/02/2010 | FC Oss | - | Helmond Sport | 0:2 |
Netherlands