| 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 | ||||
| 4. Round | 30/08/2019 | SC Cambuur | - | FC Den Bosch | 3:2 | ||||
| 6. Round | 13/09/2019 | FC Den Bosch | - | NEC Nijmegen | 2:2 | ||||
| 7. Round | 20/09/2019 | FC Den Bosch | - | MVV | 4:0 | ||||
| 13. Round | 01/11/2019 | FC Den Bosch | - | Helmond Sport | 1:1 | ||||
| 15. Round | 17/11/2019 | FC Den Bosch | - | SBV Excelsior | 3:3 |  |
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| 17. Round | 29/11/2019 | FC Den Bosch | - | FC Dordrecht | 3:2 | ||||
| 29. Round | 06/03/2020 | FC Den Bosch | - | Almere City FC | 1:2 |
Netherlands