1. Round | 16/08/2008 | KSV Roeselare | - | KV Kortrijk | 2:2 | ||||
2. Round | 23/08/2008 | Sporting Charleroi | - | KSV Roeselare | 1:0 | ||||
3. Round | 31/08/2008 | KSV Roeselare | - | Standard Liège | 1:1 | ||||
5. Round | 20/09/2008 | KSV Roeselare | - | Sporting Lokeren | 0:1 | ||||
6. Round | 27/09/2008 | RAEC Mons | - | KSV Roeselare | 2:0 | ||||
7. Round | 05/10/2008 | KSV Roeselare | - | Club Brugge KV | 0:1 | ||||
10. Round | 01/11/2008 | KV Mechelen | - | KSV Roeselare | 1:2 | ||||
11. Round | 08/11/2008 | KSV Roeselare | - | AFC Tubize | 1:2 | ||||
12. Round | 15/11/2008 | KRC Genk | - | KSV Roeselare | 1:1 | ||||
14. Round | 29/11/2008 | KAA Gent | - | KSV Roeselare | 4:0 | ||||
15. Round | 06/12/2008 | KSV Roeselare | - | KVC Westerlo | 1:0 | ||||
16. Round | 14/12/2008 | KSV Roeselare | - | RSC Anderlecht | 0:3 | ||||
17. Round | 20/12/2008 | Cercle Brugge | - | KSV Roeselare | 4:3 | ||||
27. Round | 21/03/2009 | KSV Roeselare | - | KV Mechelen | 1:0 |