| 3. Round | 01/09/1989 | FC Carl Zeiss Jena | - | HFC Chemie | 2:0 |  |
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| 4. Round | 09/09/1989 | FC Karl-Marx-Stadt | - | FC Carl Zeiss Jena | 3:0 | ||||
| 5. Round | 16/09/1989 | FC Carl Zeiss Jena | - | Dynamo Dresden | 1:1 | ||||
| 6. Round | 22/09/1989 | FC Carl Zeiss Jena | - | Hansa Rostock | 2:1 | ||||
| 7. Round | 13/10/1989 | BFC Dynamo | - | FC Carl Zeiss Jena | 2:0 | ||||
| 8. Round | 20/10/1989 | FC Carl Zeiss Jena | - | Stahl Eisenhüttenstadt | 1:1 | ||||
| 9. Round | 28/10/1989 | 1. FC Lokomotive Leipzig | - | FC Carl Zeiss Jena | 1:0 | ||||
| 13. Round | 02/12/1989 | BSG Stahl Brandenburg | - | FC Carl Zeiss Jena | 4:0 |
Germany