| 4. Round | 10/08/2018 | Karlsruher SC | - | FC Carl Zeiss Jena | 1:1 |  |
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| 5. Round | 27/08/2018 | FC Carl Zeiss Jena | - | FSV Zwickau | 2:1 | ||||
| 16. Round | 24/11/2018 | FC Carl Zeiss Jena | - | SpVgg Unterhaching | 4:5 | ||||
| 17. Round | 01/12/2018 | Würzburger Kickers | - | FC Carl Zeiss Jena | 5:2 | ||||
| 18. Round | 07/12/2018 | FC Carl Zeiss Jena | - | SV Meppen | 1:2 | |
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| 19. Round | 16/12/2018 | TSV 1860 München | - | FC Carl Zeiss Jena | 1:3 | ||||
| 20. Round | 23/12/2018 | SG Sonnenhof Großaspach | - | FC Carl Zeiss Jena | 0:0 | ||||
| 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 | ||||
| 24. Round | 17/02/2019 | FSV Zwickau | - | FC Carl Zeiss Jena | 2:0 | |
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| 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 | ||||
| 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