| 11. Round | 18/10/2019 | Telstar | - | Almere City FC | 1:0 | ||||
| 12. Round | 25/10/2019 | Helmond Sport | - | Telstar | 1:4 | ||||
| 13. Round | 01/11/2019 | Telstar | - | FC Utrecht (J) | 2:0 | ||||
| 14. Round | 08/11/2019 | Jong PSV | - | Telstar | 1:1 |  |
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| 15. Round | 17/11/2019 | Telstar | - | Go Ahead Eagles | 0:2 | |
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| 16. Round | 22/11/2019 | FC Dordrecht | - | Telstar | 2:3 | ||||
| 17. Round | 29/11/2019 | Telstar | - | Jong Ajax | 2:3 | |
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| 18. Round | 06/12/2019 | Telstar | - | NAC Breda | 1:1 | |
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| 19. Round | 13/12/2019 | De Graafschap | - | Telstar | 2:2 | ||||
| 20. Round | 22/12/2019 | Telstar | - | AZ Alkmaar (J) | 3:1 | ||||
| 21. Round | 10/01/2020 | Telstar | - | FC Eindhoven | 2:0 | ||||
| 22. Round | 17/01/2020 | SBV Excelsior | - | Telstar | 3:3 |  |
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| 23. Round | 24/01/2020 | Telstar | - | TOP Oss | 1:0 | |
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| 25. Round | 07/02/2020 | Telstar | - | NEC Nijmegen | 1:7 | ||||
| 26. Round | 14/02/2020 | FC Volendam | - | Telstar | 1:1 | |
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| 27. Round | 21/02/2020 | Telstar | - | MVV | 2:1 | ||||
| 28. Round | 28/02/2020 | Jong Ajax | - | Telstar | 2:2 | ||||
| 29. Round | 06/03/2020 | Telstar | - | Jong PSV | 1:0 |
Netherlands