| 14. Round | 23/11/2019 | Hallescher FC [Youth B] | - | 1. FC Union Berlin [Youth B] | 0:2 |  |
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| 15. Round | 01/12/2019 | 1. FC Union Berlin [Youth B] | - | Werder Bremen [Youth B] | 3:5 | ||||
| 16. Round | 07/12/2019 | Hertha BSC [Youth B] | - | 1. FC Union Berlin [Youth B] | 2:1 | ||||
| 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 | ||||
| 20. Round | 01/03/2020 | Dynamo Dresden [Youth B] | - | 1. FC Union Berlin [Youth B] | 0:2 | ||||
| 21. Round | 08/03/2020 | 1. FC Union Berlin [Youth B] | - | Hannover 96 [Youth B] | 2:1 |
Germany