| 1. Round | 14/08/1999 | HFC Haarlem | - | FC Volendam | 2:2 | ||||
| 2. Round | 21/08/1999 | Dordrecht '90 | - | HFC Haarlem | 2:0 | ||||
| 3. Round | 28/08/1999 | Helmond Sport | - | HFC Haarlem | 1:0 | ||||
| 5. Round | 11/09/1999 | RBC Roosendaal | - | HFC Haarlem | 2:1 |  |
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| 11. Round | 01/11/1999 | TOP Oss | - | HFC Haarlem | 2:1 | ||||
| 13. Round | 20/11/1999 | NAC Breda | - | HFC Haarlem | 6:1 | |
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| 14. Round | 27/11/1999 | HFC Haarlem | - | Heracles Almelo | 2:2 | |
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| 15. Round | 06/12/1999 | BV Emmen | - | HFC Haarlem | 1:4 | ||||
| 17. Round | 18/12/1999 | FC Groningen | - | HFC Haarlem | 4:2 | ||||
| 16. Round | 22/12/1999 | HFC Haarlem | - | Go Ahead Eagles | 1:4 | ||||
| 19. Round | 29/01/2000 | HFC Haarlem | - | Dordrecht '90 | 2:4 | ||||
| 20. Round | 05/02/2000 | HFC Haarlem | - | Helmond Sport | 1:2 | |
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| 21. Round | 12/02/2000 | SBV Excelsior | - | HFC Haarlem | 4:0 | ||||
| 24. Round | 04/03/2000 | HFC Haarlem | - | FC Zwolle | 0:2 | ||||
| 18. Round | 08/03/2000 | FC Volendam | - | HFC Haarlem | 1:0 | ||||
| 25. Round | 11/03/2000 | BV Veendam | - | HFC Haarlem | 2:3 | |
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| 27. Round | 25/03/2000 | VVV | - | HFC Haarlem | 2:2 |  |
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| 29. Round | 09/04/2000 | Telstar | - | HFC Haarlem | 1:2 | ||||
| 30. Round | 15/04/2000 | HFC Haarlem | - | NAC Breda | 0:1 | |
Netherlands