| 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 | ||||
| 4. Round | 13/09/2008 | Germinal Beerschot | - | KSV Roeselare | 3:0 | ||||
| 7. Round | 05/10/2008 | KSV Roeselare | - | Club Brugge KV | 0:1 | ||||
| 8. Round | 18/10/2008 | Excelsior Mouscron | - | KSV Roeselare | 2:0 | ||||
| 11. Round | 08/11/2008 | KSV Roeselare | - | AFC Tubize | 1:2 | ||||
| 14. Round | 29/11/2008 | KAA Gent | - | KSV Roeselare | 4:0 |
Belgium