| 1. Round | 13/08/1988 | Dynamo Dresden | - | Rot-Weiß Erfurt | 2:0 | ||||
| 2. Round | 20/08/1988 | 1. FC Magdeburg | - | Dynamo Dresden | 0:2 | ||||
| 3. Round | 27/08/1988 | Dynamo Dresden | - | FC Karl-Marx-Stadt | 3:4 | ||||
| 4. Round | 03/09/1988 | Dynamo Dresden | - | BSG Stahl Brandenburg | 3:1 | ||||
| 8. Round | 12/10/1988 | Dynamo Dresden | - | BSG Energie Cottbus | 5:1 | ||||
| 10. Round | 04/11/1988 | Dynamo Dresden | - | Hansa Rostock | 5:0 | ||||
| 11. Round | 12/11/1988 | HFC Chemie | - | Dynamo Dresden | 1:3 | ||||
| 13. Round | 03/12/1988 | 1. FC Union Berlin | - | Dynamo Dresden | 1:3 | ||||
| 15. Round | 04/03/1989 | Dynamo Dresden | - | 1. FC Magdeburg | 0:0 | ||||
| 18. Round | 11/03/1989 | Dynamo Dresden | - | BSG Sachsenring Zwickau | 4:1 | ||||
| 16. Round | 18/03/1989 | FC Karl-Marx-Stadt | - | Dynamo Dresden | 2:1 | ||||
| 17. Round | 25/03/1989 | BSG Stahl Brandenburg | - | Dynamo Dresden | 2:2 | ||||
| 20. Round | 31/03/1989 | Dynamo Dresden | - | 1. FC Lokomotive Leipzig | 3:0 | ||||
| 21. Round | 29/04/1989 | BSG Energie Cottbus | - | Dynamo Dresden | 0:1 | ||||
| 19. Round | 03/05/1989 | BFC Dynamo | - | Dynamo Dresden | 1:1 |
Germany