| 1. Round | 12/08/2019 | Jong PSV | - | FC Den Bosch | 2:2 | ||||
| 2. Round | 16/08/2019 | FC Den Bosch | - | Telstar | 0:1 | ||||
| 3. Round | 23/08/2019 | FC Den Bosch | - | FC Eindhoven | 1:1 | ||||
| 6. Round | 13/09/2019 | FC Den Bosch | - | NEC Nijmegen | 2:2 | ||||
| 5. Round | 16/09/2019 | FC Utrecht (J) | - | FC Den Bosch | 5:1 | ||||
| 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 | ||||
| 10. Round | 13/10/2019 | FC Volendam | - | FC Den Bosch | 1:1 |  |
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| 11. Round | 18/10/2019 | FC Den Bosch | - | Roda JC Kerkrade | 0:0 |  |
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| 28. Round | 28/02/2020 | MVV | - | FC Den Bosch | 2:3 | |
Netherlands