| 1. Round | 08/08/2008 | HFC Haarlem | - | TOP Oss | 2:1 | ||||
| 2. Round | 15/08/2008 | FC Eindhoven | - | HFC Haarlem | 3:2 | ||||
| 3. Round | 22/08/2008 | RBC Roosendaal | - | HFC Haarlem | 2:0 | ||||
| 4. Round | 31/08/2008 | HFC Haarlem | - | Telstar | 4:2 |  |
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| 5. Round | 07/09/2008 | HFC Haarlem | - | FC Dordrecht | 3:0 | |
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| 6. Round | 12/09/2008 | Fortuna Sittard | - | HFC Haarlem | 1:2 | ||||
| 7. Round | 15/09/2008 | RKC Waalwijk | - | HFC Haarlem | 1:1 | ||||
| 8. Round | 19/09/2008 | HFC Haarlem | - | FC Den Bosch | 1:4 | ||||
| 9. Round | 26/09/2008 | AGOVV | - | HFC Haarlem | 2:0 | ||||
| 10. Round | 03/10/2008 | SC Cambuur | - | HFC Haarlem | 3:2 |  |
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| 11. Round | 10/10/2008 | HFC Haarlem | - | VVV-Venlo | 0:4 | ||||
| 13. Round | 24/10/2008 | Helmond Sport | - | HFC Haarlem | 1:1 | ||||
| 17. Round | 21/11/2008 | HFC Haarlem | - | MVV | 0:3 | ||||
| 18. Round | 28/11/2008 | HFC Haarlem | - | BV Veendam | 1:0 | ||||
| 19. Round | 05/12/2008 | FC Omniworld | - | HFC Haarlem | 0:1 | ||||
| 20. Round | 12/12/2008 | TOP Oss | - | HFC Haarlem | 1:0 | ||||
| 21. Round | 19/12/2008 | HFC Haarlem | - | AGOVV | 1:0 | |
Netherlands