| 1. Round | 16/08/2008 | Cercle Brugge | - | RSC Anderlecht | 0:3 | ||||
| 2. Round | 23/08/2008 | KV Kortrijk | - | Cercle Brugge | 2:1 | ||||
| 3. Round | 30/08/2008 | Cercle Brugge | - | RAEC Mons | 2:1 | ||||
| 4. Round | 14/09/2008 | Sporting Charleroi | - | Cercle Brugge | 3:2 |  |
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| 5. Round | 20/09/2008 | Cercle Brugge | - | Germinal Beerschot | 1:0 | ||||
| 6. Round | 27/09/2008 | Sporting Lokeren | - | Cercle Brugge | 1:1 | ||||
| 7. Round | 05/10/2008 | Cercle Brugge | - | Standard Liège | 4:1 | ||||
| 8. Round | 19/10/2008 | Club Brugge KV | - | Cercle Brugge | 3:1 |  |
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| 9. Round | 25/10/2008 | Cercle Brugge | - | FCV Dender EH | 1:2 | ||||
| 10. Round | 01/11/2008 | Excelsior Mouscron | - | Cercle Brugge | 0:1 | |
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| 11. Round | 07/11/2008 | Cercle Brugge | - | SV Zulte Waregem | 2:0 | ||||
| 12. Round | 15/11/2008 | AFC Tubize | - | Cercle Brugge | 3:0 | ||||
| 13. Round | 22/11/2008 | Cercle Brugge | - | KV Mechelen | 2:1 | ||||
| 14. Round | 29/11/2008 | KRC Genk | - | Cercle Brugge | 3:2 | |
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| 15. Round | 05/12/2008 | Cercle Brugge | - | KAA Gent | 3:1 | |
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| 16. Round | 13/12/2008 | KVC Westerlo | - | Cercle Brugge | 1:2 | |
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| 17. Round | 20/12/2008 | Cercle Brugge | - | KSV Roeselare | 4:3 | |
Belgium