1. Round | 17/08/1968 | 1. FC Union Berlin | - | Hansa Rostock | 3:4 | ||||
2. Round | 24/08/1968 | BSG Sachsenring Zwickau | - | 1. FC Union Berlin | 0:1 | ||||
3. Round | 31/08/1968 | 1. FC Union Berlin | - | BSG Stahl Riesa | 2:0 | ||||
4. Round | 07/09/1968 | Rot-Weiß Erfurt | - | 1. FC Union Berlin | 0:0 | ||||
5. Round | 14/09/1968 | 1. FC Union Berlin | - | FC Karl-Marx-Stadt | 1:2 | ||||
7. Round | 28/09/1968 | 1. FC Union Berlin | - | 1. FC Magdeburg | 3:3 | ||||
8. Round | 05/10/1968 | BSG Wismut Aue | - | 1. FC Union Berlin | 2:0 | ||||
9. Round | 12/10/1968 | 1. FC Union Berlin | - | HFC Chemie | 0:1 | ||||
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 |