| 14. Round | 30/11/2008 | Club Brugge KV | - | Germinal Beerschot | 3:0 | ||||
| 15. Round | 07/12/2008 | Sporting Lokeren | - | Club Brugge KV | 2:0 | ||||
| 16. Round | 14/12/2008 | Club Brugge KV | - | Standard Liège | 1:4 | ||||
| 17. Round | 20/12/2008 | Excelsior Mouscron | - | Club Brugge KV | 5:1 |  |
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| 18. Round | 17/01/2009 | Club Brugge KV | - | KV Mechelen | 3:0 | ||||
| 20. Round | 31/01/2009 | Club Brugge KV | - | AFC Tubize | 3:1 |  |
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| 21. Round | 07/02/2009 | FCV Dender EH | - | Club Brugge KV | 0:2 | ||||
| 23. Round | 22/02/2009 | KVC Westerlo | - | Club Brugge KV | 1:1 | ||||
| 24. Round | 28/02/2009 | Club Brugge KV | - | KSV Roeselare | 2:1 | ||||
| 25. Round | 08/03/2009 | Cercle Brugge | - | Club Brugge KV | 1:3 | ||||
| 26. Round | 15/03/2009 | Club Brugge KV | - | KAA Gent | 1:4 | |
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| 27. Round | 20/03/2009 | KV Kortrijk | - | Club Brugge KV | 2:3 | |
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| 29. Round | 12/04/2009 | RSC Anderlecht | - | Club Brugge KV | 1:0 | ||||
| 33. Round | 09/05/2009 | Standard Liège | - | Club Brugge KV | 2:0 | |
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| 34. Round | 16/05/2009 | Club Brugge KV | - | Excelsior Mouscron | 4:1 |
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