| 3. Round | 16/08/2023 | SV Babelsberg 03 | - | FC Carl Zeiss Jena | 2:1 | ||||
| 4. Round | 20/08/2023 | FC Carl Zeiss Jena | - | 1. FC Lok Leipzig | 2:3 | ||||
| 5. Round | 25/08/2023 | BFC Dynamo | - | FC Carl Zeiss Jena | 2:1 | ||||
| 6. Round | 02/09/2023 | FC Carl Zeiss Jena | - | FSV 63 Luckenwalde | 3:0 |  |
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| 7. Round | 16/09/2023 | Hertha BSC II | - | FC Carl Zeiss Jena | 1:1 | |
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| 8. Round | 23/09/2023 | FC Carl Zeiss Jena | - | FC Viktoria 1889 Berlin | 1:2 | ||||
| 9. Round | 01/10/2023 | Rot-Weiß Erfurt | - | FC Carl Zeiss Jena | 1:1 | ||||
| 10. Round | 07/10/2023 | FC Carl Zeiss Jena | - | Hansa Rostock II | 5:1 | ||||
| 11. Round | 21/10/2023 | Energie Cottbus | - | FC Carl Zeiss Jena | 0:2 | |
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| 12. Round | 29/10/2023 | FC Carl Zeiss Jena | - | BSG Chemie Leipzig | 1:0 |  |
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| 16. Round | 02/12/2023 | FC Carl Zeiss Jena | - | ZFC Meuselwitz | 1:0 | ||||
| 18. Round | 16/12/2023 | FC Carl Zeiss Jena | - | Chemnitzer FC | 0:1 | ||||
| 19. Round | 28/01/2024 | Greifswalder FC | - | FC Carl Zeiss Jena | 3:0 |
Germany