1. Round | 08/08/2008 | SBV Excelsior | - | Telstar | 0:1 | ||||
2. Round | 15/08/2008 | Telstar | - | FC Den Bosch | 2:2 | ||||
3. Round | 22/08/2008 | Telstar | - | TOP Oss | 2:2 | ||||
4. Round | 31/08/2008 | HFC Haarlem | - | Telstar | 4:2 | ||||
5. Round | 05/09/2008 | FC Zwolle | - | Telstar | 3:0 | ||||
6. Round | 12/09/2008 | Telstar | - | RKC Waalwijk | 1:2 | ||||
9. Round | 27/09/2008 | Telstar | - | Helmond Sport | 2:3 | ||||
10. Round | 03/10/2008 | Telstar | - | FC Eindhoven | 1:1 | ||||
11. Round | 10/10/2008 | MVV | - | Telstar | 2:0 | ||||
12. Round | 17/10/2008 | VVV-Venlo | - | Telstar | 1:0 | ||||
13. Round | 26/10/2008 | Telstar | - | Go Ahead Eagles | 4:1 | ||||
14. Round | 31/10/2008 | Fortuna Sittard | - | Telstar | 2:1 | ||||
15. Round | 07/11/2008 | Telstar | - | FC Omniworld | 3:1 | ||||
18. Round | 28/11/2008 | FC Dordrecht | - | Telstar | 1:1 | ||||
24. Round | 30/01/2009 | TOP Oss | - | Telstar | 3:0 |