| 4. Round | 24/08/2019 | FC St. Pauli [Youth B] | - | 1. FC Union Berlin [Youth B] | 2:4 | ||||
| 14. Round | 23/11/2019 | Hallescher FC [Youth B] | - | 1. FC Union Berlin [Youth B] | 0:2 |  |
|||
| 15. Round | 01/12/2019 | 1. FC Union Berlin [Youth B] | - | Werder Bremen [Youth B] | 3:5 | |
 |
||
| 17. Round | 14/12/2019 | 1. FC Union Berlin [Youth B] | - | FC St. Pauli [Youth B] | 3:4 |  |
|||
| 18. Round | 15/02/2020 | Energie Cottbus [Youth B] | - | 1. FC Union Berlin [Youth B] | 3:3 | ||||
| 19. Round | 22/02/2020 | 1. FC Union Berlin [Youth B] | - | FC Carl Zeiss Jena [Youth B] | 4:3 | |
|||
| 21. Round | 08/03/2020 | 1. FC Union Berlin [Youth B] | - | Hannover 96 [Youth B] | 2:1 |
Germany