| 2. Round | 16/11/1968 | BSG Motor Grimma | - | FC Carl Zeiss Jena | 1:1 aet |  |
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| 2. Round | 20/11/1968 | FC Carl Zeiss Jena | - | BSG Motor Grimma | 10:1 | |
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| Round of 16 | 30/11/1968 | 1. FC Union Berlin | - | FC Carl Zeiss Jena | 0:1 | ||||
| Quarter-finals | 23/04/1969 | FC Vorwärts Berlin | - | FC Carl Zeiss Jena | 4:1 |
Germany