| 1. Round | 10/08/2019 | Hertha BSC [Youth B] | - | Chemnitzer FC [Youth B] | 3:1 |  |
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| 2. Round | 17/08/2019 | Chemnitzer FC [Youth B] | - | Energie Cottbus [Youth B] | 0:0 | ||||
| 3. Round | 21/08/2019 | Dynamo Dresden [Youth B] | - | Chemnitzer FC [Youth B] | 2:1 | ||||
| 10. Round | 19/10/2019 | Chemnitzer FC [Youth B] | - | Hannover 96 [Youth B] | 0:3 | ||||
| 11. Round | 26/10/2019 | Eintracht Braunschweig [Youth B] | - | Chemnitzer FC [Youth B] | 2:1 | ||||
| 12. Round | 02/11/2019 | 1. FC Union Berlin [Youth B] | - | Chemnitzer FC [Youth B] | 1:1 | ||||
| 13. Round | 09/11/2019 | Hallescher FC [Youth B] | - | Chemnitzer FC [Youth B] | 1:3 | ||||
| 17. Round | 14/12/2019 | VfL Wolfsburg [Youth B] | - | Chemnitzer FC [Youth B] | 3:0 | ||||
| 18. Round | 15/02/2020 | Chemnitzer FC [Youth B] | - | Hamburger SV [Youth B] | 1:0 | ||||
| 19. Round | 22/02/2020 | RB Leipzig [Youth B] | - | Chemnitzer FC [Youth B] | 4:0 | |
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| 20. Round | 29/02/2020 | Chemnitzer FC [Youth B] | - | Werder Bremen [Youth B] | 3:2 | ||||
| 21. Round | 07/03/2020 | FC St. Pauli [Youth B] | - | Chemnitzer FC [Youth B] | 1:2 |
Germany