| 10. Round | 22/10/1999 | Willem II | - | MVV | 1:0 | ||||
| 12. Round | 05/11/1999 | De Graafschap | - | Willem II | 0:2 | ||||
| 13. Round | 19/11/1999 | Willem II | - | Roda JC Kerkrade | 2:2 | ||||
| 21. Round | 08/02/2000 | Willem II | - | NEC Nijmegen | 3:1 | ||||
| 22. Round | 12/02/2000 | AFC Ajax | - | Willem II | 3:1 | ||||
| 23. Round | 19/02/2000 | Willem II | - | Feyenoord | 2:1 | ||||
| 23. Round | 25/02/2000 | Fortuna Sittard | - | Willem II | 2:0 | ||||
| 24. Round | 02/03/2000 | AZ Alkmaar | - | Willem II | 2:2 | ||||
| 25. Round | 10/03/2000 | Willem II | - | sc Heerenveen | 2:3 |
Netherlands