1. Round | 11/08/1999 | Sparta Rotterdam | - | Willem II | 0:2 | ||||
2. Round | 20/08/1999 | Willem II | - | Fortuna Sittard | 2:2 | ||||
3. Round | 27/08/1999 | Willem II | - | FC Den Bosch | 2:1 | ||||
4. Round | 10/09/1999 | sc Heerenveen | - | Willem II | 2:4 | ||||
5. Round | 17/09/1999 | Willem II | - | AZ Alkmaar | 3:1 | ||||
7. Round | 02/10/1999 | Willem II | - | AFC Ajax | 3:6 | ||||
8. Round | 11/10/1999 | SC Cambuur | - | Willem II | 0:1 | ||||
9. Round | 15/10/1999 | Willem II | - | RKC Waalwijk | 2:1 | ||||
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 | ||||
14. Round | 26/11/1999 | FC Twente | - | Willem II | 4:0 | ||||
15. Round | 30/11/1999 | Feyenoord | - | Willem II | 1:0 | ||||
16. Round | 04/12/1999 | Willem II | - | FC Utrecht | 4:3 | ||||
17. Round | 14/12/1999 | Vitesse | - | Willem II | 3:1 | ||||
17. Round | 17/12/1999 | Willem II | - | Sparta Rotterdam | 0:0 | ||||
33. Round | 06/05/2000 | Willem II | - | SC Cambuur | 1:4 |