| 3. Round | 22/08/2008 | SBV Excelsior | - | Fortuna Sittard | 5:1 | ||||
| 4. Round | 28/08/2008 | Fortuna Sittard | - | TOP Oss | 1:1 | ||||
| 5. Round | 05/09/2008 | BV Veendam | - | Fortuna Sittard | 0:0 | ||||
| 6. Round | 12/09/2008 | Fortuna Sittard | - | HFC Haarlem | 1:2 | ||||
| 7. Round | 15/09/2008 | FC Den Bosch | - | Fortuna Sittard | 1:1 |  |
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| 8. Round | 19/09/2008 | Fortuna Sittard | - | FC Omniworld | 2:0 | ||||
| 9. Round | 26/09/2008 | Fortuna Sittard | - | RBC Roosendaal | 0:0 | ||||
| 10. Round | 03/10/2008 | Helmond Sport | - | Fortuna Sittard | 2:2 | ||||
| 12. Round | 17/10/2008 | Fortuna Sittard | - | SC Cambuur | 1:4 | |
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| 13. Round | 24/10/2008 | FC Dordrecht | - | Fortuna Sittard | 3:0 | |
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| 14. Round | 31/10/2008 | Fortuna Sittard | - | Telstar | 2:1 | ||||
| 17. Round | 21/11/2008 | Fortuna Sittard | - | AGOVV | 2:4 |  |
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| 19. Round | 05/12/2008 | Fortuna Sittard | - | FC Eindhoven | 2:1 | |
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| 20. Round | 12/12/2008 | FC Emmen | - | Fortuna Sittard | 1:2 | ||||
| 21. Round | 19/12/2008 | RBC Roosendaal | - | Fortuna Sittard | 0:1 | ||||
| 23. Round | 27/01/2009 | SC Cambuur | - | Fortuna Sittard | 2:1 | ||||
| 38. Round | 08/05/2009 | Telstar | - | Fortuna Sittard | 1:1 |
Belgium