| 1. Round | 17/08/1968 | 1. FC Magdeburg | - | FC Karl-Marx-Stadt | 3:1 | ||||
| 6. Round | 21/09/1968 | FC Karl-Marx-Stadt | - | FC Vorwärts Berlin | 2:2 | ||||
| 7. Round | 28/09/1968 | 1. FC Lokomotive Leipzig | - | 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 | ||||
| 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 | ||||
| 14. Round | 15/02/1969 | FC Karl-Marx-Stadt | - | 1. FC Magdeburg | 3:0 | ||||
| 15. Round | 22/02/1969 | BSG Wismut Aue | - | FC Karl-Marx-Stadt | 1:2 | ||||
| 17. Round | 12/03/1969 | FC Carl Zeiss Jena | - | FC Karl-Marx-Stadt | 2:0 | ||||
| 24. Round | 03/05/1969 | FC Karl-Marx-Stadt | - | Rot-Weiß Erfurt | 0:0 | ||||
| 25. Round | 10/05/1969 | FC Karl-Marx-Stadt | - | BFC Dynamo | 1:2 |
Germany