| 2. Round | 15/08/2008 | RBC Roosendaal | - | FC Zwolle | 1:3 | ||||
| 3. Round | 22/08/2008 | RBC Roosendaal | - | HFC Haarlem | 2:0 |  |
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| 11. Round | 10/10/2008 | RBC Roosendaal | - | AGOVV | 3:0 | |
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| 12. Round | 17/10/2008 | Go Ahead Eagles | - | RBC Roosendaal | 1:0 | ||||
| 13. Round | 24/10/2008 | RBC Roosendaal | - | SC Cambuur | 1:2 | ||||
| 14. Round | 31/10/2008 | FC Den Bosch | - | RBC Roosendaal | 2:1 | |
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| 15. Round | 07/11/2008 | RBC Roosendaal | - | RKC Waalwijk | 2:2 | ||||
| 22. Round | 16/01/2009 | VVV-Venlo | - | RBC Roosendaal | 3:1 | ||||
| 27. Round | 20/02/2009 | RBC Roosendaal | - | Telstar | 1:0 |
Czech Republic