| 1. Round | 05/08/1989 | BSG Chemie Velten | - | 1. FC Union Berlin | 2:2 | ||||
| 3. Round | 19/08/1989 | KWO Berlin | - | 1. FC Union Berlin | 0:1 | ||||
| 4. Round | 01/09/1989 | 1. FC Union Berlin | - | BSG Bergmann Borsig | 2:2 | ||||
| 5. Round | 09/09/1989 | BSG Schiffahrt/Hafen Rostock | - | 1. FC Union Berlin | 2:0 | ||||
| 9. Round | 15/10/1989 | BSG Aktivist Schwarze Pumpe Hoyerswerda | - | 1. FC Union Berlin | 0:1 | ||||
| 16. Round | 09/12/1989 | Dynamo Fürstenwalde | - | 1. FC Union Berlin | 0:1 | ||||
| 17. Round | 15/12/1989 | 1. FC Union Berlin | - | Chemie Guben | 1:0 |
Germany