| 18. Round | 17/01/2009 | KV Kortrijk | - | KSV Roeselare | 2:1 | ||||
| 19. Round | 24/01/2009 | KSV Roeselare | - | Sporting Charleroi | 3:1 |  |
|||
| 20. Round | 31/01/2009 | Standard Liège | - | KSV Roeselare | 3:0 |  |
|||
| 21. Round | 07/02/2009 | KSV Roeselare | - | Germinal Beerschot | 2:2 | ||||
| 22. Round | 14/02/2009 | Sporting Lokeren | - | KSV Roeselare | 2:1 | ||||
| 23. Round | 21/02/2009 | KSV Roeselare | - | RAEC Mons | 3:2 | |
|
||
| 24. Round | 28/02/2009 | Club Brugge KV | - | KSV Roeselare | 2:1 | |
|||
| 25. Round | 07/03/2009 | KSV Roeselare | - | Excelsior Mouscron | 2:0 | |
|||
| 26. Round | 14/03/2009 | SV Zulte Waregem | - | KSV Roeselare | 0:0 | ||||
| 27. Round | 21/03/2009 | KSV Roeselare | - | KV Mechelen | 1:0 | ||||
| 28. Round | 04/04/2009 | AFC Tubize | - | KSV Roeselare | 0:1 | ||||
| 29. Round | 10/04/2009 | KSV Roeselare | - | KRC Genk | 1:0 | ||||
| 30. Round | 19/04/2009 | FCV Dender EH | - | KSV Roeselare | 3:1 | ||||
| 31. Round | 26/04/2009 | KSV Roeselare | - | KAA Gent | 1:3 | ||||
| 32. Round | 02/05/2009 | KVC Westerlo | - | KSV Roeselare | 1:0 | |
|||
| 33. Round | 09/05/2009 | RSC Anderlecht | - | KSV Roeselare | 3:1 | ||||
| 34. Round | 16/05/2009 | KSV Roeselare | - | Cercle Brugge | 1:2 | |
Croatia
