| 1. Round | 09/08/2019 | TOP Oss | - | Jong Ajax | 2:1 | ||||
| 2. Round | 19/08/2019 | FC Utrecht (J) | - | TOP Oss | 2:1 | ||||
| 3. Round | 23/08/2019 | TOP Oss | - | AZ Alkmaar (J) | 1:2 | ||||
| 4. Round | 30/08/2019 | TOP Oss | - | De Graafschap | 0:0 | ||||
| 5. Round | 08/09/2019 | Roda JC Kerkrade | - | TOP Oss | 2:1 | ||||
| 6. Round | 14/09/2019 | TOP Oss | - | Go Ahead Eagles | 1:2 | ||||
| 7. Round | 21/09/2019 | Helmond Sport | - | TOP Oss | 0:2 | ||||
| 8. Round | 27/09/2019 | TOP Oss | - | NAC Breda | 0:1 | ||||
| 9. Round | 04/10/2019 | FC Den Bosch | - | TOP Oss | 4:0 | ||||
| 20. Round | 20/12/2019 | Jong Ajax | - | TOP Oss | 2:0 | ||||
| 21. Round | 13/01/2020 | AZ Alkmaar (J) | - | TOP Oss | 3:1 |  |
|||
| 22. Round | 17/01/2020 | TOP Oss | - | SC Cambuur | 3:2 |
Spain