| 1. Round | 10/08/2019 | Hertha BSC [Youth B] | - | Chemnitzer FC [Youth B] | 3:1 | ||||
| 3. Round | 21/08/2019 | Dynamo Dresden [Youth B] | - | Chemnitzer FC [Youth B] | 2:1 | ||||
| 5. Round | 31/08/2019 | Hamburger SV [Youth B] | - | Chemnitzer FC [Youth B] | 4:1 | ||||
| 7. Round | 21/09/2019 | Werder Bremen [Youth B] | - | Chemnitzer FC [Youth B] | 2:0 | ||||
| 8. Round | 28/09/2019 | Chemnitzer FC [Youth B] | - | FC St. Pauli [Youth B] | 4:0 | ||||
| 10. Round | 19/10/2019 | Chemnitzer FC [Youth B] | - | Hannover 96 [Youth B] | 0:3 | ||||
| 14. Round | 23/11/2019 | Chemnitzer FC [Youth B] | - | Hertha BSC [Youth B] | 0:5 | ||||
| 17. Round | 14/12/2019 | VfL Wolfsburg [Youth B] | - | Chemnitzer FC [Youth B] | 3:0 | ||||
| 19. Round | 22/02/2020 | RB Leipzig [Youth B] | - | Chemnitzer FC [Youth B] | 4:0 | ||||
| 21. Round | 07/03/2020 | FC St. Pauli [Youth B] | - | Chemnitzer FC [Youth B] | 1:2 |
Germany