| 1. Round | 12/08/1989 | Dynamo Dresden | - | HFC Chemie | 2:0 | ||||
| 2. Round | 19/08/1989 | BSG Fortschritt Bischofswerda | - | Dynamo Dresden | 0:1 | ||||
| 3. Round | 01/09/1989 | FC Karl-Marx-Stadt | - | Dynamo Dresden | 1:1 | ||||
| 4. Round | 09/09/1989 | Dynamo Dresden | - | BSG Wismut Aue | 3:0 |  |
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| 5. Round | 16/09/1989 | FC Carl Zeiss Jena | - | Dynamo Dresden | 1:1 | ||||
| 6. Round | 22/09/1989 | Dynamo Dresden | - | Rot-Weiß Erfurt | 3:1 | ||||
| 7. Round | 13/10/1989 | Hansa Rostock | - | Dynamo Dresden | 0:0 | ||||
| 8. Round | 20/10/1989 | Dynamo Dresden | - | BSG Stahl Brandenburg | 3:2 | |
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| 9. Round | 28/10/1989 | BFC Dynamo | - | Dynamo Dresden | 1:1 | ||||
| 10. Round | 08/11/1989 | Dynamo Dresden | - | 1. FC Magdeburg | 3:1 | ||||
| 13. Round | 05/12/1989 | 1. FC Lokomotive Leipzig | - | Dynamo Dresden | 1:1 | |
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| 17. Round | 17/03/1990 | BSG Wismut Aue | - | Dynamo Dresden | 1:1 | ||||
| 18. Round | 23/03/1990 | Dynamo Dresden | - | FC Carl Zeiss Jena | 0:4 | ||||
| 19. Round | 03/04/1990 | Rot-Weiß Erfurt | - | Dynamo Dresden | 2:0 | |
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Germany