| 17. Round | 21/11/2008 | TOP Oss | - | RBC Roosendaal | 0:3 | ||||
| 18. Round | 28/11/2008 | RBC Roosendaal | - | Helmond Sport | 1:1 | ||||
| 19. Round | 05/12/2008 | FC Dordrecht | - | RBC Roosendaal | 1:1 | ||||
| 20. Round | 12/12/2008 | RBC Roosendaal | - | FC Omniworld | 1:1 | ||||
| 21. Round | 19/12/2008 | RBC Roosendaal | - | Fortuna Sittard | 0:1 | ||||
| 22. Round | 16/01/2009 | VVV-Venlo | - | RBC Roosendaal | 3:1 | ||||
| 23. Round | 23/01/2009 | RBC Roosendaal | - | Go Ahead Eagles | 0:1 | ||||
| 24. Round | 03/02/2009 | HFC Haarlem | - | RBC Roosendaal | 2:0 | ||||
| 25. Round | 06/02/2009 | RBC Roosendaal | - | BV Veendam | 2:1 | ||||
| 37. Round | 01/05/2009 | RKC Waalwijk | - | RBC Roosendaal | 3:1 | ||||
| 38. Round | 08/05/2009 | RBC Roosendaal | - | FC Den Bosch | 0:1 |
Netherlands