| 1. Round | 11/08/2019 | Dynamo Dresden [Youth] | - | Werder Bremen [Youth] | 0:2 | ||||
| 5. Round | 14/09/2019 | Dynamo Dresden [Youth] | - | Hannover 96 [Youth] | 4:6 | ||||
| 9. Round | 26/10/2019 | Dynamo Dresden [Youth] | - | Hamburger SV [Youth] | 0:4 | ||||
| 10. Round | 02/11/2019 | RB Leipzig [Youth] | - | Dynamo Dresden [Youth] | 2:2 | ||||
| 12. Round | 23/11/2019 | Dynamo Dresden [Youth] | - | VfL Wolfsburg [Youth] | 2:0 | ||||
| 13. Round | 30/11/2019 | FC St. Pauli [Youth] | - | Dynamo Dresden [Youth] | 1:3 | ||||
| 17. Round | 15/02/2020 | Dynamo Dresden [Youth] | - | Energie Cottbus [Youth] | 2:3 |  |
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| 18. Round | 22/02/2020 | Hannover 96 [Youth] | - | Dynamo Dresden [Youth] | 4:1 | |
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| 19. Round | 29/02/2020 | Dynamo Dresden [Youth] | - | Niendorfer TSV [Youth] | 1:0 | ||||
| 20. Round | 07/03/2020 | 1. FC Union Berlin [Youth] | - | Dynamo Dresden [Youth] | 6:0 | |
Germany