| 1. Round | 16/08/2008 | KVC Westerlo | - | Sporting Charleroi | 1:0 | ||||
| 3. Round | 31/08/2008 | KAA Gent | - | Sporting Charleroi | 2:0 | ||||
| 4. Round | 14/09/2008 | Sporting Charleroi | - | Cercle Brugge | 3:2 | ||||
| 5. Round | 19/09/2008 | RSC Anderlecht | - | Sporting Charleroi | 2:0 | ||||
| 6. Round | 27/09/2008 | Sporting Charleroi | - | KV Kortrijk | 1:2 |  |
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| 12. Round | 15/11/2008 | Excelsior Mouscron | - | Sporting Charleroi | 2:1 | ||||
| 13. Round | 22/11/2008 | Sporting Charleroi | - | AFC Tubize | 3:2 | ||||
| 14. Round | 29/11/2008 | SV Zulte Waregem | - | Sporting Charleroi | 4:2 | ||||
| 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 | ||||
| 19. Round | 24/01/2009 | KSV Roeselare | - | Sporting Charleroi | 3:1 |
France
Congo DR