| 10. Round | 23/10/1999 | FC Groningen | - | Telstar | 5:0 | ||||
| 11. Round | 30/10/1999 | Telstar | - | FC Volendam | 3:1 | ||||
| 13. Round | 20/11/1999 | Telstar | - | Helmond Sport | 1:0 | ||||
| 15. Round | 04/12/1999 | Telstar | - | RBC Roosendaal | 2:4 | ||||
| 16. Round | 11/12/1999 | SBV Eindhoven | - | Telstar | 3:0 | ||||
| 17. Round | 18/12/1999 | Telstar | - | FC Zwolle | 0:4 |  |
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| 19. Round | 29/01/2000 | ADO Den Haag | - | Telstar | 1:4 | ||||
| 21. Round | 12/02/2000 | TOP Oss | - | Telstar | 2:1 | |
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| 24. Round | 04/03/2000 | Heracles Almelo | - | Telstar | 2:1 | ||||
| 25. Round | 11/03/2000 | Telstar | - | BV Emmen | 0:1 | ||||
| 26. Round | 18/03/2000 | Go Ahead Eagles | - | Telstar | 3:0 | ||||
| 27. Round | 25/03/2000 | Telstar | - | FC Groningen | 0:2 | |
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| 28. Round | 01/04/2000 | FC Volendam | - | Telstar | 0:3 | |
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| 30. Round | 15/04/2000 | Helmond Sport | - | Telstar | 2:0 | ||||
| 31. Round | 22/04/2000 | Telstar | - | SBV Excelsior | 1:1 |  |
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| 32. Round | 01/05/2000 | RBC Roosendaal | - | Telstar | 3:2 | ||||
| 33. Round | 06/05/2000 | Telstar | - | SBV Eindhoven | 2:1 | ||||
| 34. Round | 13/05/2000 | FC Zwolle | - | Telstar | 3:3 | |
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Netherlands