| 21. Round | 26/01/2019 | FC Carl Zeiss Jena | - | Preußen Münster | 0:0 | ||||
| 22. Round | 02/02/2019 | Hallescher FC | - | FC Carl Zeiss Jena | 0:0 | ||||
| 23. Round | 09/02/2019 | FC Carl Zeiss Jena | - | Karlsruher SC | 1:1 |  |
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| 24. Round | 17/02/2019 | FSV Zwickau | - | FC Carl Zeiss Jena | 2:0 | ||||
| 26. Round | 03/03/2019 | FC Carl Zeiss Jena | - | Eintracht Braunschweig | 0:0 | |
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| 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 | |
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| 30. Round | 23/03/2019 | FC Carl Zeiss Jena | - | KFC Uerdingen 05 | 0:0 | ||||
| 31. Round | 31/03/2019 | VfR Aalen | - | FC Carl Zeiss Jena | 1:1 | ||||
| 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 | ||||
| 35. Round | 28/04/2019 | SpVgg Unterhaching | - | FC Carl Zeiss Jena | 0:1 | |
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| 36. Round | 04/05/2019 | FC Carl Zeiss Jena | - | Würzburger Kickers | 3:4 | ||||
| 37. Round | 11/05/2019 | SV Meppen | - | FC Carl Zeiss Jena | 0:1 | ||||
| 38. Round | 18/05/2019 | FC Carl Zeiss Jena | - | TSV 1860 München | 4:0 |
Germany