| 1. Round | 17/08/2018 | RKC Waalwijk | - | Telstar | 1:0 | ||||
| 3. Round | 31/08/2018 | Telstar | - | FC Utrecht (J) | 2:0 | ||||
| 4. Round | 07/09/2018 | FC Dordrecht | - | Telstar | 1:4 |  |
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| 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 | |
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| 8. Round | 05/10/2018 | Jong Ajax | - | Telstar | 3:0 | |
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| 9. Round | 12/10/2018 | Helmond Sport | - | Telstar | 1:2 |  |
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| 10. Round | 19/10/2018 | Telstar | - | NEC Nijmegen | 0:3 | ||||
| 12. Round | 04/11/2018 | Telstar | - | Go Ahead Eagles | 2:1 | |
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| 13. Round | 09/11/2018 | FC Eindhoven | - | Telstar | 1:2 | ||||
| 14. Round | 18/11/2018 | Telstar | - | FC Den Bosch | 1:4 | |
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| 15. Round | 23/11/2018 | Roda JC Kerkrade | - | Telstar | 3:0 | ||||
| 16. Round | 30/11/2018 | Telstar | - | Almere City FC | 1:1 | |
England