| 3. Round | 27/08/1988 | FC Carl Zeiss Jena | - | Hansa Rostock | 2:0 | ||||
| 6. Round | 24/09/1988 | 1. FC Union Berlin | - | FC Carl Zeiss Jena | 1:1 |  |
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| 7. Round | 30/09/1988 | FC Carl Zeiss Jena | - | Rot-Weiß Erfurt | 3:0 | |
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| 8. Round | 12/10/1988 | 1. FC Magdeburg | - | FC Carl Zeiss Jena | 0:2 | |
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| 11. Round | 12/11/1988 | FC Carl Zeiss Jena | - | BSG Sachsenring Zwickau | 2:0 | ||||
| 16. Round | 17/03/1989 | Hansa Rostock | - | FC Carl Zeiss Jena | 2:0 | ||||
| 18. Round | 05/04/1989 | BSG Wismut Aue | - | FC Carl Zeiss Jena | 2:0 | ||||
| 22. Round | 06/05/1989 | Dynamo Dresden | - | FC Carl Zeiss Jena | 1:1 |
Germany