| 1. Round | 10/08/2019 | 1. FC Union Berlin [Youth B] | - | Hallescher FC [Youth B] | 3:1 |  |
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| 3. Round | 21/08/2019 | Energie Cottbus [Youth B] | - | Hallescher FC [Youth B] | 1:0 | ||||
| 4. Round | 25/08/2019 | Hallescher FC [Youth B] | - | Dynamo Dresden [Youth B] | 2:1 | ||||
| 6. Round | 14/09/2019 | Hallescher FC [Youth B] | - | Hamburger SV [Youth B] | 2:4 | ||||
| 9. Round | 05/10/2019 | FC St. Pauli [Youth B] | - | Hallescher FC [Youth B] | 2:1 | ||||
| 12. Round | 02/11/2019 | Eintracht Braunschweig [Youth B] | - | Hallescher FC [Youth B] | 0:3 | ||||
| 13. Round | 09/11/2019 | Hallescher FC [Youth B] | - | Chemnitzer FC [Youth B] | 1:3 | ||||
| 14. Round | 23/11/2019 | Hallescher FC [Youth B] | - | 1. FC Union Berlin [Youth B] | 0:2 | |
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| 16. Round | 07/12/2019 | Hallescher FC [Youth B] | - | Energie Cottbus [Youth B] | 0:2 | ||||
| 17. Round | 14/12/2019 | Dynamo Dresden [Youth B] | - | Hallescher FC [Youth B] | 1:1 | ||||
| 18. Round | 15/02/2020 | Hallescher FC [Youth B] | - | VfL Wolfsburg [Youth B] | 1:5 | |
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| 20. Round | 29/02/2020 | Hallescher FC [Youth B] | - | RB Leipzig [Youth B] | 0:1 | ||||
| 21. Round | 08/03/2020 | Werder Bremen [Youth B] | - | Hallescher FC [Youth B] | 2:1 |
Germany