| 1. Round | 16/08/2008 | KSV Roeselare | - | KV Kortrijk | 2:2 | ||||
| 3. Round | 31/08/2008 | KSV Roeselare | - | Standard Liège | 1:1 |  |
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| 6. Round | 27/09/2008 | RAEC Mons | - | KSV Roeselare | 2:0 | ||||
| 7. Round | 05/10/2008 | KSV Roeselare | - | Club Brugge KV | 0:1 | ||||
| 8. Round | 18/10/2008 | Excelsior Mouscron | - | KSV Roeselare | 2:0 | ||||
| 12. Round | 15/11/2008 | KRC Genk | - | KSV Roeselare | 1:1 | ||||
| 17. Round | 20/12/2008 | Cercle Brugge | - | KSV Roeselare | 4:3 |
Belgium