| 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 | ||||
| 7. Round | 21/09/2019 | Helmond Sport | - | TOP Oss | 0:2 | ||||
| 8. Round | 27/09/2019 | TOP Oss | - | NAC Breda | 0:1 | ||||
| 10. Round | 12/10/2019 | TOP Oss | - | Telstar | 2:2 | ||||
| 11. Round | 18/10/2019 | SC Cambuur | - | TOP Oss | 5:1 | ||||
| 16. Round | 22/11/2019 | MVV | - | TOP Oss | 4:0 | ||||
| 17. Round | 29/11/2019 | TOP Oss | - | FC Eindhoven | 3:1 | ||||
| 18. Round | 06/12/2019 | Almere City FC | - | TOP Oss | 3:0 |
Netherlands