| 3. Round | 29/08/2008 | AFC Tubize | - | Club Brugge KV | 1:4 | ||||
| 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 | ||||
| 8. Round | 19/10/2008 | Club Brugge KV | - | Cercle Brugge | 3:1 | ||||
| 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 | ||||
| 25. Round | 08/03/2009 | Cercle Brugge | - | Club Brugge KV | 1:3 | ||||
| 28. Round | 04/04/2009 | Club Brugge KV | - | Sporting Charleroi | 2:1 | ||||
| 29. Round | 12/04/2009 | RSC Anderlecht | - | Club Brugge KV | 1:0 | ||||
| 30. Round | 18/04/2009 | Club Brugge KV | - | RAEC Mons | 3:2 | ||||
| 31. Round | 24/04/2009 | Germinal Beerschot | - | Club Brugge KV | 2:0 |  |
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| 32. Round | 01/05/2009 | Club Brugge KV | - | Sporting Lokeren | 2:3 | |
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| 33. Round | 09/05/2009 | Standard Liège | - | Club Brugge KV | 2:0 | ||||
| 34. Round | 16/05/2009 | Club Brugge KV | - | Excelsior Mouscron | 4:1 |
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