| 5. Round | 14/09/2008 | KVK Tienen | - | KMSK Deinze | 4:2 |  |
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| 7. Round | 27/09/2008 | KMSK Deinze | - | KVSK United | 3:1 | |
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| 8. Round | 04/10/2008 | KAS Eupen | - | KMSK Deinze | 2:2 | |
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| 13. Round | 08/11/2008 | KMSK Deinze | - | FC Brussels | 1:1 | |
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| 14. Round | 15/11/2008 | Excelsior Virton | - | KMSK Deinze | 2:2 | |
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| 22. Round | 17/01/2009 | KMSK Deinze | - | KV Oostende | 3:3 | |
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| 30. Round | 14/03/2009 | KSK Beveren | - | KMSK Deinze | 1:1 | |
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| 37. Round | 26/04/2009 | KMSK Deinze | - | Royal Antwerp FC | 1:3 | |
Belgium