| 1. Round | 13/08/2023 | VfL Osnabrück [Youth] | - | 1. FC Union Berlin [Youth] | 0:0 | ||||
| 2. Round | 19/08/2023 | 1. FC Union Berlin [Youth] | - | Dynamo Dresden [Youth] | 5:1 |  |
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| 3. Round | 23/08/2023 | Hertha BSC [Youth] | - | 1. FC Union Berlin [Youth] | 3:0 | ||||
| 4. Round | 27/08/2023 | 1. FC Union Berlin [Youth] | - | RB Leipzig [Youth] | 5:1 | ||||
| 5. Round | 16/09/2023 | 1. FC Union Berlin [Youth] | - | Hansa Rostock [Youth] | 2:1 | ||||
| 8. Round | 21/10/2023 | Werder Bremen [Youth] | - | 1. FC Union Berlin [Youth] | 0:4 | ||||
| 9. Round | 29/10/2023 | 1. FC Union Berlin [Youth] | - | FC St. Pauli [Youth] | 3:1 |  |
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| 10. Round | 04/11/2023 | Hamburger SV [Youth] | - | 1. FC Union Berlin [Youth] | 1:1 | ||||
| 11. Round | 12/11/2023 | 1. FC Union Berlin [Youth] | - | VfL Wolfsburg [Youth] | 1:0 | |
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| 12. Round | 25/11/2023 | Hannover 96 [Youth] | - | 1. FC Union Berlin [Youth] | 5:1 | ||||
| 13. Round | 27/01/2024 | 1. FC Union Berlin [Youth] | - | FC Carl Zeiss Jena [Youth] | 4:2 | ||||
| 15. Round | 03/02/2024 | Dynamo Dresden [Youth] | - | 1. FC Union Berlin [Youth] | 0:4 | ||||
| 17. Round | 17/02/2024 | RB Leipzig [Youth] | - | 1. FC Union Berlin [Youth] | 1:1 |
Germany