| 1. Round | 12/08/2019 | Jong PSV | - | FC Den Bosch | 2:2 |  |
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| 2. Round | 16/08/2019 | FC Den Bosch | - | Telstar | 0:1 |  |
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| 3. Round | 23/08/2019 | FC Den Bosch | - | FC Eindhoven | 1:1 | ||||
| 4. Round | 30/08/2019 | SC Cambuur | - | FC Den Bosch | 3:2 |  |
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| 7. Round | 20/09/2019 | FC Den Bosch | - | MVV | 4:0 | ||||
| 8. Round | 30/09/2019 | AZ Alkmaar (J) | - | FC Den Bosch | 2:2 | ||||
| 9. Round | 04/10/2019 | FC Den Bosch | - | TOP Oss | 4:0 | |
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| 10. Round | 13/10/2019 | FC Volendam | - | FC Den Bosch | 1:1 | ||||
| 11. Round | 18/10/2019 | FC Den Bosch | - | Roda JC Kerkrade | 0:0 | ||||
| 12. Round | 25/10/2019 | Go Ahead Eagles | - | FC Den Bosch | 0:0 | ||||
| 13. Round | 01/11/2019 | FC Den Bosch | - | Helmond Sport | 1:1 | ||||
| 14. Round | 08/11/2019 | Jong Ajax | - | FC Den Bosch | 5:1 | ||||
| 16. Round | 22/11/2019 | Almere City FC | - | FC Den Bosch | 0:2 | ||||
| 17. Round | 29/11/2019 | FC Den Bosch | - | FC Dordrecht | 3:2 | ||||
| 18. Round | 06/12/2019 | FC Den Bosch | - | De Graafschap | 2:2 | ||||
| 19. Round | 13/12/2019 | NAC Breda | - | FC Den Bosch | 1:2 | ||||
| 20. Round | 20/12/2019 | FC Den Bosch | - | Jong PSV | 2:1 | ||||
| 21. Round | 12/01/2020 | NEC Nijmegen | - | FC Den Bosch | 1:0 | ||||
| 29. Round | 06/03/2020 | FC Den Bosch | - | Almere City FC | 1:2 |
Netherlands