| 1. Round | 17/08/1968 | FC Carl Zeiss Jena | - | BSG Sachsenring Zwickau | 0:1 | ||||
| 3. Round | 31/08/1968 | FC Carl Zeiss Jena | - | Rot-Weiß Erfurt | 1:0 | ||||
| 4. Round | 07/09/1968 | FC Karl-Marx-Stadt | - | FC Carl Zeiss Jena | 1:0 | ||||
| 6. Round | 21/09/1968 | 1. FC Magdeburg | - | FC Carl Zeiss Jena | 0:0 | ||||
| 7. Round | 28/09/1968 | FC Carl Zeiss Jena | - | BSG Wismut Aue | 1:0 | ||||
| 8. Round | 05/10/1968 | HFC Chemie | - | FC Carl Zeiss Jena | 1:1 | ||||
| 9. Round | 12/10/1968 | FC Carl Zeiss Jena | - | BFC Dynamo | 4:0 | ||||
| 10. Round | 23/10/1968 | FC Carl Zeiss Jena | - | 1. FC Union Berlin | 6:0 | ||||
| 11. Round | 26/10/1968 | FC Vorwärts Berlin | - | FC Carl Zeiss Jena | 1:0 | ||||
| 12. Round | 02/11/1968 | FC Carl Zeiss Jena | - | 1. FC Lokomotive Leipzig | 3:0 | ||||
| 13. Round | 09/11/1968 | Hansa Rostock | - | FC Carl Zeiss Jena | 4:1 | ||||
| 14. Round | 15/02/1969 | BSG Sachsenring Zwickau | - | FC Carl Zeiss Jena | 0:0 |
Germany