| 1. Round | 17/08/2018 | RKC Waalwijk | - | Telstar | 1:0 |  |
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| 2. Round | 24/08/2018 | Telstar | - | MVV | 0:1 | ||||
| 4. Round | 07/09/2018 | FC Dordrecht | - | Telstar | 1:4 | ||||
| 5. Round | 14/09/2018 | SC Cambuur | - | Telstar | 2:0 | ||||
| 6. Round | 21/09/2018 | Telstar | - | FC Twente | 1:3 | ||||
| 7. Round | 28/09/2018 | Telstar | - | TOP Oss | 1:0 | ||||
| 8. Round | 05/10/2018 | Jong Ajax | - | Telstar | 3:0 | ||||
| 15. Round | 23/11/2018 | Roda JC Kerkrade | - | Telstar | 3:0 | ||||
| 17. Round | 10/12/2018 | AZ Alkmaar (J) | - | Telstar | 0:2 | ||||
| 18. Round | 14/12/2018 | Telstar | - | Jong PSV | 2:4 | ||||
| 19. Round | 21/12/2018 | FC Volendam | - | Telstar | 1:0 | ||||
| 20. Round | 13/01/2019 | Telstar | - | Helmond Sport | 1:1 | ||||
| 21. Round | 18/01/2019 | NEC Nijmegen | - | Telstar | 1:1 | ||||
| 22. Round | 25/01/2019 | Telstar | - | Sparta Rotterdam | 1:1 | ||||
| 23. Round | 01/02/2019 | MVV | - | Telstar | 2:0 | ||||
| 30. Round | 22/03/2019 | FC Den Bosch | - | Telstar | 3:4 | ||||
| 32. Round | 01/04/2019 | Go Ahead Eagles | - | Telstar | 2:3 | ||||
| 36. Round | 22/04/2019 | Telstar | - | Roda JC Kerkrade | 4:0 | ||||
| 37. Round | 26/04/2019 | Telstar | - | FC Volendam | 1:1 | ||||
| 38. Round | 03/05/2019 | Jong PSV | - | Telstar | 2:0 |
Netherlands