| 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 | ||||
| 5. Round | 14/09/1968 | 1. FC Union Berlin | - | FC Karl-Marx-Stadt | 1:2 | ||||
| 25. Round | 10/05/1969 | FC Karl-Marx-Stadt | - | BFC Dynamo | 1:2 | ||||
| 26. Round | 17/05/1969 | BSG Chemie Leipzig | - | FC Karl-Marx-Stadt | 1:1 |
Germany