| 2. Round | 14/09/2008 | NAC Breda | - | Willem II | 1:3 | ||||
| 3. Round | 19/09/2008 | FC Utrecht | - | Willem II | 1:0 | ||||
| 4. Round | 27/09/2008 | Willem II | - | AZ Alkmaar | 2:5 | ||||
| 5. Round | 04/10/2008 | Vitesse | - | Willem II | 2:2 | ||||
| 6. Round | 19/10/2008 | Willem II | - | Feyenoord | 1:0 | ||||
| 7. Round | 25/10/2008 | Willem II | - | De Graafschap | 1:1 | ||||
| 8. Round | 28/10/2008 | FC Volendam | - | Willem II | 2:2 |  |
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| 9. Round | 01/11/2008 | PSV Eindhoven | - | Willem II | 2:0 | |
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| 13. Round | 29/11/2008 | Heracles Almelo | - | Willem II | 1:0 | ||||
| 15. Round | 13/12/2008 | Willem II | - | NEC Nijmegen | 1:2 | ||||
| 16. Round | 21/12/2008 | FC Twente | - | Willem II | 2:0 |
Belgium