| 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 | ||||
| 15. Round | 12/11/2018 | SV Wehen Wiesbaden | - | FC Carl Zeiss Jena | 2:3 | ||||
| 16. Round | 24/11/2018 | FC Carl Zeiss Jena | - | SpVgg Unterhaching | 4:5 |  |
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| 17. Round | 01/12/2018 | Würzburger Kickers | - | FC Carl Zeiss Jena | 5:2 | ||||
| 21. Round | 26/01/2019 | FC Carl Zeiss Jena | - | Preußen Münster | 0:0 | ||||
| 25. Round | 23/02/2019 | FC Carl Zeiss Jena | - | Fortuna Köln | 0:1 | ||||
| 27. Round | 10/03/2019 | 1. FC Kaiserslautern | - | FC Carl Zeiss Jena | 4:1 | ||||
| 28. Round | 13/03/2019 | FC Carl Zeiss Jena | - | Sportfreunde Lotte | 1:1 | ||||
| 29. Round | 16/03/2019 | VfL Osnabrück | - | FC Carl Zeiss Jena | 3:1 | ||||
| 30. Round | 23/03/2019 | FC Carl Zeiss Jena | - | KFC Uerdingen 05 | 0:0 | ||||
| 32. Round | 06/04/2019 | FC Carl Zeiss Jena | - | Energie Cottbus | 2:1 | ||||
| 33. Round | 13/04/2019 | Hansa Rostock | - | FC Carl Zeiss Jena | 1:2 | ||||
| 34. Round | 20/04/2019 | FC Carl Zeiss Jena | - | SV Wehen Wiesbaden | 3:1 |
Germany