| 2. Round | 23/08/2008 | Sporting Charleroi | - | KSV Roeselare | 1:0 | ||||
| 7. Round | 04/10/2008 | RAEC Mons | - | Sporting Charleroi | 1:1 | ||||
| 8. Round | 18/10/2008 | Germinal Beerschot | - | Sporting Charleroi | 1:2 | ||||
| 9. Round | 25/10/2008 | Sporting Charleroi | - | Sporting Lokeren | 1:1 | ||||
| 16. Round | 13/12/2008 | KRC Genk | - | Sporting Charleroi | 1:0 | ||||
| 17. Round | 20/12/2008 | Sporting Charleroi | - | FCV Dender EH | 2:0 |  |
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| 18. Round | 18/01/2009 | Sporting Charleroi | - | KVC Westerlo | 1:2 |  |
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| 19. Round | 24/01/2009 | KSV Roeselare | - | Sporting Charleroi | 3:1 | ||||
| 20. Round | 01/02/2009 | Sporting Charleroi | - | KAA Gent | 2:5 | ||||
| 21. Round | 08/02/2009 | Cercle Brugge | - | Sporting Charleroi | 2:2 | ||||
| 23. Round | 21/02/2009 | KV Kortrijk | - | Sporting Charleroi | 1:1 | ||||
| 24. Round | 28/02/2009 | Sporting Charleroi | - | RAEC Mons | 3:0 |
Belgium
Italy