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 | ||||
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 | ||||
14. Round | 15/02/1969 | Hansa Rostock | - | 1. FC Union Berlin | 1:1 | ||||
15. Round | 22/02/1969 | 1. FC Union Berlin | - | BSG Sachsenring Zwickau | 2:3 | ||||
16. Round | 01/03/1969 | BSG Stahl Riesa | - | 1. FC Union Berlin | 1:0 | ||||
25. Round | 10/05/1969 | FC Vorwärts Berlin | - | 1. FC Union Berlin | 2:0 |