| 3. Round | 29/08/2008 | AFC Tubize | - | Club Brugge KV | 1:4 |  |
|||
| 4. Round | 13/09/2008 | Club Brugge KV | - | FCV Dender EH | 1:1 |  |
|||
| 5. Round | 21/09/2008 | KRC Genk | - | Club Brugge KV | 0:1 | ||||
| 1. Round | 24/09/2008 | KV Mechelen | - | Club Brugge KV | 1:1 | ||||
| 6. Round | 27/09/2008 | Club Brugge KV | - | KVC Westerlo | 2:0 | ||||
| 7. Round | 05/10/2008 | KSV Roeselare | - | Club Brugge KV | 0:1 | ||||
| 9. Round | 26/10/2008 | KAA Gent | - | Club Brugge KV | 3:0 | ||||
| 2. Round | 29/10/2008 | Club Brugge KV | - | SV Zulte Waregem | 2:0 | ||||
| 10. Round | 01/11/2008 | Club Brugge KV | - | KV Kortrijk | 4:1 | ||||
| 11. Round | 09/11/2008 | Sporting Charleroi | - | Club Brugge KV | 2:2 | |
|||
| 17. Round | 20/12/2008 | Excelsior Mouscron | - | Club Brugge KV | 5:1 | ||||
| 18. Round | 17/01/2009 | Club Brugge KV | - | KV Mechelen | 3:0 | ||||
| 19. Round | 25/01/2009 | SV Zulte Waregem | - | Club Brugge KV | 3:1 | ||||
| 20. Round | 31/01/2009 | Club Brugge KV | - | AFC Tubize | 3:1 | |
|||
| 21. Round | 07/02/2009 | FCV Dender EH | - | Club Brugge KV | 0:2 | |
|||
| 22. Round | 15/02/2009 | Club Brugge KV | - | KRC Genk | 0:2 |
Peru