| 1. Round | 14/08/1999 | BV Veendam | - | Telstar | 2:2 | ||||
| 3. Round | 28/08/1999 | VVV | - | Telstar | 1:0 | ||||
| 4. Round | 05/09/1999 | Telstar | - | TOP Oss | 3:0 | ||||
| 5. Round | 11/09/1999 | Telstar | - | Dordrecht '90 | 0:3 | ||||
| 2. Round | 15/09/1999 | Telstar | - | ADO Den Haag | 2:0 |  |
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| 6. Round | 18/09/1999 | NAC Breda | - | Telstar | 2:0 | ||||
| 7. Round | 27/09/1999 | Telstar | - | Heracles Almelo | 0:2 | ||||
| 8. Round | 02/10/1999 | BV Emmen | - | Telstar | 2:0 | ||||
| 9. Round | 16/10/1999 | Telstar | - | Go Ahead Eagles | 0:3 | ||||
| 10. Round | 23/10/1999 | FC Groningen | - | Telstar | 5:0 | ||||
| 11. Round | 30/10/1999 | Telstar | - | FC Volendam | 3:1 | ||||
| 12. Round | 07/11/1999 | HFC Haarlem | - | Telstar | 1:3 | ||||
| 13. Round | 20/11/1999 | Telstar | - | Helmond Sport | 1:0 | ||||
| 14. Round | 27/11/1999 | SBV Excelsior | - | Telstar | 0:2 | ||||
| 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 |
Netherlands