| 22. Round | 16/01/2009 | Fortuna Sittard | - | Helmond Sport | 3:1 | ||||
| 23. Round | 23/01/2009 | Helmond Sport | - | BV Veendam | 1:3 |  |
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| 24. Round | 30/01/2009 | Helmond Sport | - | MVV | 2:1 | ||||
| 25. Round | 06/02/2009 | FC Eindhoven | - | Helmond Sport | 1:1 |  |
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| 26. Round | 13/02/2009 | Helmond Sport | - | FC Emmen | 3:1 | ||||
| 27. Round | 20/02/2009 | FC Dordrecht | - | Helmond Sport | 1:0 | ||||
| 28. Round | 28/02/2009 | Helmond Sport | - | Go Ahead Eagles | 1:1 | |
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| 29. Round | 06/03/2009 | HFC Haarlem | - | Helmond Sport | 1:3 | ||||
| 30. Round | 13/03/2009 | VVV-Venlo | - | Helmond Sport | 2:0 | ||||
| 32. Round | 27/03/2009 | RKC Waalwijk | - | Helmond Sport | 3:0 | |
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| 33. Round | 03/04/2009 | Helmond Sport | - | FC Omniworld | 1:0 | ||||
| 34. Round | 10/04/2009 | SC Cambuur | - | Helmond Sport | 2:0 | ||||
| 35. Round | 17/04/2009 | Helmond Sport | - | FC Den Bosch | 3:0 | |
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| 36. Round | 24/04/2009 | TOP Oss | - | Helmond Sport | 1:2 | ||||
| 37. Round | 01/05/2009 | Helmond Sport | - | FC Zwolle | 0:0 |
Netherlands