| 4. Round | 07/09/2018 | Helmond Sport | - | FC Den Bosch | 0:2 | ||||
| 5. Round | 16/09/2018 | Sparta Rotterdam | - | FC Den Bosch | 2:0 | ||||
| 7. Round | 28/09/2018 | FC Den Bosch | - | AZ Alkmaar (J) | 3:1 |  |
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| 8. Round | 05/10/2018 | MVV | - | FC Den Bosch | 0:3 | ||||
| 9. Round | 12/10/2018 | FC Den Bosch | - | FC Dordrecht | 1:0 |  |
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| 19. Round | 22/12/2018 | FC Den Bosch | - | Roda JC Kerkrade | 2:0 | ||||
| 20. Round | 13/01/2019 | FC Dordrecht | - | FC Den Bosch | 2:6 | ||||
| 21. Round | 18/01/2019 | FC Den Bosch | - | TOP Oss | 3:0 | ||||
| 25. Round | 15/02/2019 | AZ Alkmaar (J) | - | FC Den Bosch | 0:0 | ||||
| 26. Round | 22/02/2019 | FC Den Bosch | - | MVV | 1:2 | ||||
| 27. Round | 01/03/2019 | Jong Ajax | - | FC Den Bosch | 2:2 | ||||
| 28. Round | 08/03/2019 | FC Den Bosch | - | Helmond Sport | 3:0 | ||||
| 30. Round | 22/03/2019 | FC Den Bosch | - | Telstar | 3:4 | |
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| 31. Round | 29/03/2019 | FC Twente | - | FC Den Bosch | 1:0 | |
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| 32. Round | 01/04/2019 | FC Den Bosch | - | Jong PSV | 3:1 | ||||
| 33. Round | 05/04/2019 | FC Den Bosch | - | Sparta Rotterdam | 1:1 | ||||
| 34. Round | 12/04/2019 | Almere City FC | - | FC Den Bosch | 3:1 |
Netherlands
Morocco