| 1. Round | 28/07/2018 | FC Carl Zeiss Jena | - | SG Sonnenhof Großaspach | 3:2 | ||||
| 2. Round | 04/08/2018 | Preußen Münster | - | FC Carl Zeiss Jena | 1:2 | ||||
| 3. Round | 07/08/2018 | FC Carl Zeiss Jena | - | Hallescher FC | 0:3 | ||||
| 7. Round | 14/09/2018 | Eintracht Braunschweig | - | FC Carl Zeiss Jena | 2:0 | ||||
| 8. Round | 22/09/2018 | FC Carl Zeiss Jena | - | 1. FC Kaiserslautern | 3:3 |  |
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| 9. Round | 25/09/2018 | Sportfreunde Lotte | - | FC Carl Zeiss Jena | 2:0 | ||||
| 10. Round | 30/09/2018 | FC Carl Zeiss Jena | - | VfL Osnabrück | 0:0 | ||||
| 11. Round | 06/10/2018 | KFC Uerdingen 05 | - | FC Carl Zeiss Jena | 2:1 | ||||
| 12. Round | 19/10/2018 | FC Carl Zeiss Jena | - | VfR Aalen | 0:0 | ||||
| 13. Round | 27/10/2018 | Energie Cottbus | - | FC Carl Zeiss Jena | 2:1 | ||||
| 14. Round | 03/11/2018 | FC Carl Zeiss Jena | - | Hansa Rostock | 1:1 | ||||
| 18. Round | 07/12/2018 | FC Carl Zeiss Jena | - | SV Meppen | 1:2 | ||||
| 25. Round | 23/02/2019 | FC Carl Zeiss Jena | - | Fortuna Köln | 0:1 |
Germany