| 1. Round | 26/07/2019 | 1. FC Lok Leipzig | - | Hertha BSC II | 2:1 | ||||
| 2. Round | 30/07/2019 | Hertha BSC II | - | Energie Cottbus | 5:2 | ||||
| 3. Round | 03/08/2019 | VfB Auerbach | - | Hertha BSC II | 1:5 | ||||
| 9. Round | 21/09/2019 | BSG Chemie Leipzig | - | Hertha BSC II | 1:3 | ||||
| 10. Round | 28/09/2019 | Hertha BSC II | - | SV Babelsberg 03 | 3:3 | ||||
| 12. Round | 20/10/2019 | Hertha BSC II | - | Union Fürstenwalde | 4:1 | ||||
| 14. Round | 01/11/2019 | Hertha BSC II | - | SV Lichtenberg 47 | 2:4 | ||||
| 15. Round | 09/11/2019 | VSG Altglienicke | - | Hertha BSC II | 3:0 | ||||
| 19. Round | 14/12/2019 | Energie Cottbus | - | Hertha BSC II | 3:1 | ||||
| 20. Round | 02/02/2020 | Hertha BSC II | - | VfB Auerbach | 1:2 | ||||
| 21. Round | 07/02/2020 | Optik Rathenow | - | Hertha BSC II | 0:2 | ||||
| 24. Round | 28/02/2020 | Hertha BSC II | - | BFC Dynamo | 4:7 |
Germany