| 1. Round | 07/08/2009 | SBV Excelsior | - | Telstar | 2:2 | ||||
| 2. Round | 14/08/2009 | Telstar | - | FC Oss | 1:1 | ||||
| 3. Round | 21/08/2009 | Telstar | - | Helmond Sport | 1:4 | ||||
| 4. Round | 24/08/2009 | RBC Roosendaal | - | Telstar | 0:3 | ||||
| 5. Round | 28/08/2009 | BV Veendam | - | Telstar | 1:1 | ||||
| 7. Round | 11/09/2009 | De Graafschap | - | Telstar | 2:1 |  |
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| 8. Round | 18/09/2009 | Telstar | - | FC Emmen | 4:1 | ||||
| 9. Round | 25/09/2009 | FC Eindhoven | - | Telstar | 1:2 |  |
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| 12. Round | 16/10/2009 | Telstar | - | FC Den Bosch | 1:4 | ||||
| 13. Round | 23/10/2009 | FC Dordrecht | - | Telstar | 0:3 | |
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| 14. Round | 30/10/2009 | FC Omniworld | - | Telstar | 2:1 | ||||
| 15. Round | 06/11/2009 | Telstar | - | FC Zwolle | 2:3 | ||||
| 18. Round | 27/11/2009 | Telstar | - | Fortuna Sittard | 3:1 | ||||
| 19. Round | 30/11/2009 | SC Cambuur | - | Telstar | 1:1 | ||||
| 20. Round | 04/12/2009 | FC Den Bosch | - | Telstar | 2:0 | ||||
| 21. Round | 11/12/2009 | Telstar | - | FC Dordrecht | 1:3 | |
Finland