| 1. Round | 17/08/1968 | 1. FC Magdeburg | - | FC Karl-Marx-Stadt | 3:1 | ||||
| 2. Round | 24/08/1968 | FC Karl-Marx-Stadt | - | BSG Wismut Aue | 2:3 | ||||
| 3. Round | 31/08/1968 | HFC Chemie | - | FC Karl-Marx-Stadt | 2:0 | ||||
| 4. Round | 07/09/1968 | FC Karl-Marx-Stadt | - | FC Carl Zeiss Jena | 1:0 | ||||
| 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 | ||||
| 13. Round | 09/11/1968 | FC Karl-Marx-Stadt | - | BSG Chemie Leipzig | 1:0 | ||||
| 18. Round | 15/03/1969 | FC Karl-Marx-Stadt | - | 1. FC Union Berlin | 2:2 | ||||
| 21. Round | 05/04/1969 | Hansa Rostock | - | FC Karl-Marx-Stadt | 1:2 | ||||
| 23. Round | 26/04/1969 | BSG Stahl Riesa | - | FC Karl-Marx-Stadt | 2:1 |
Germany