| 3. Round | 31/08/1968 | 1. FC Union Berlin | - | BSG Stahl Riesa | 2:0 | ||||
| 7. Round | 28/09/1968 | 1. FC Union Berlin | - | 1. FC Magdeburg | 3:3 | ||||
| 9. Round | 12/10/1968 | 1. FC Union Berlin | - | HFC Chemie | 0:1 | ||||
| 10. Round | 23/10/1968 | FC Carl Zeiss Jena | - | 1. FC Union Berlin | 6:0 | ||||
| 11. Round | 26/10/1968 | 1. FC Union Berlin | - | BFC Dynamo | 1:1 | ||||
| 12. Round | 02/11/1968 | 1. FC Union Berlin | - | FC Vorwärts Berlin | 0:2 | ||||
| 24. Round | 03/05/1969 | BFC Dynamo | - | 1. FC Union Berlin | 1:1 | ||||
| 25. Round | 10/05/1969 | FC Vorwärts Berlin | - | 1. FC Union Berlin | 2:0 | ||||
| 26. Round | 17/05/1969 | 1. FC Union Berlin | - | 1. FC Lokomotive Leipzig | 1:1 |
Germany