| 1. Round | 10/08/2019 | Hamburger SV [Youth B] | - | FC St. Pauli [Youth B] | 3:1 | ||||
| 2. Round | 17/08/2019 | FC St. Pauli [Youth B] | - | RB Leipzig [Youth B] | 2:3 | ||||
| 4. Round | 24/08/2019 | FC St. Pauli [Youth B] | - | 1. FC Union Berlin [Youth B] | 2:4 | ||||
| 14. Round | 23/11/2019 | FC St. Pauli [Youth B] | - | Hamburger SV [Youth B] | 0:3 | ||||
| 15. Round | 30/11/2019 | RB Leipzig [Youth B] | - | FC St. Pauli [Youth B] | 6:1 | ||||
| 3. Round | 08/12/2019 | Werder Bremen [Youth B] | - | FC St. Pauli [Youth B] | 4:2 | ||||
| 17. Round | 14/12/2019 | 1. FC Union Berlin [Youth B] | - | FC St. Pauli [Youth B] | 3:4 |
Germany