| 5. Round | 14/09/1968 | 1. FC Union Berlin | - | FC Karl-Marx-Stadt | 1:2 | ||||
| 8. Round | 05/10/1968 | FC Karl-Marx-Stadt | - | Hansa Rostock | 3:4 | ||||
| 9. Round | 12/10/1968 | BSG Sachsenring Zwickau | - | FC Karl-Marx-Stadt | 0:1 |  |
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| 10. Round | 23/10/1968 | FC Karl-Marx-Stadt | - | BSG Stahl Riesa | 3:1 | ||||
| 11. Round | 26/10/1968 | Rot-Weiß Erfurt | - | FC Karl-Marx-Stadt | 1:0 | ||||
| 12. Round | 02/11/1968 | BFC Dynamo | - | FC Karl-Marx-Stadt | 1:0 | ||||
| 22. Round | 19/04/1969 | FC Karl-Marx-Stadt | - | BSG Sachsenring Zwickau | 1:1 |
Germany