| 1. Round | 22/08/1998 | AFC Ajax | - | Willem II | 2:0 |  |
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| 2. Round | 27/08/1998 | Roda JC Kerkrade | - | AFC Ajax | 0:2 | ||||
| 3. Round | 08/09/1998 | AFC Ajax | - | AZ Alkmaar | 5:1 | ||||
| 4. Round | 12/09/1998 | FC Utrecht | - | AFC Ajax | 2:2 | ||||
| 5. Round | 19/09/1998 | AFC Ajax | - | De Graafschap | 1:1 | ||||
| 13. Round | 10/11/1998 | AFC Ajax | - | Roda JC Kerkrade | 2:1 | ||||
| 14. Round | 14/11/1998 | AFC Ajax | - | PSV Eindhoven | 2:2 | ||||
| 15. Round | 21/11/1998 | RKC Waalwijk | - | AFC Ajax | 0:1 | |
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| 16. Round | 28/11/1998 | Vitesse | - | AFC Ajax | 3:2 | |
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| 17. Round | 05/12/1998 | AFC Ajax | - | MVV | 1:1 | ||||
| 18. Round | 12/12/1998 | AFC Ajax | - | sc Heerenveen | 0:0 | ||||
| 19. Round | 19/12/1998 | Feyenoord | - | AFC Ajax | 1:1 | ||||
| 20. Round | 13/02/1999 | FC Twente | - | AFC Ajax | 2:1 | ||||
| 20. Round | 16/02/1999 | sc Heerenveen | - | AFC Ajax | 2:2 | ||||
| 22. Round | 27/02/1999 | AFC Ajax | - | Sparta Rotterdam | 5:1 | ||||
| 23. Round | 06/03/1999 | AFC Ajax | - | FC Utrecht | 5:2 | ||||
| 24. Round | 15/03/1999 | MVV | - | AFC Ajax | 1:4 |  |
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| 26. Round | 20/03/1999 | AFC Ajax | - | Vitesse | 0:1 | |
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| 33. Round | 15/05/1999 | AFC Ajax | - | RKC Waalwijk | 2:0 |
Netherlands