| 1. Round | 13/08/1999 | PSV Eindhoven | - | MVV | 4:1 |  |
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| 2. Round | 19/08/1999 | MVV | - | AFC Ajax | 2:6 |  |
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| 3. Round | 27/08/1999 | Vitesse | - | MVV | 6:2 | |
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| 4. Round | 10/09/1999 | MVV | - | SC Cambuur | 1:1 | ||||
| 5. Round | 17/09/1999 | FC Den Bosch | - | MVV | 1:1 | |
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| 6. Round | 25/09/1999 | Sparta Rotterdam | - | MVV | 3:0 | ||||
| 6. Round | 30/09/1999 | MVV | - | sc Heerenveen | 1:3 | |
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| 7. Round | 09/10/1999 | De Graafschap | - | MVV | 2:1 | |
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| 10. Round | 22/10/1999 | Willem II | - | MVV | 1:0 | ||||
| 11. Round | 30/10/1999 | MVV | - | Fortuna Sittard | 1:0 | ||||
| 12. Round | 05/11/1999 | MVV | - | AZ Alkmaar | 3:4 | |
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| 12. Round | 18/11/1999 | MVV | - | Feyenoord | 3:3 | |
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| 18. Round | 20/12/1999 | MVV | - | PSV Eindhoven | 0:2 |
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