| 3. Round | 21/08/1965 | SC Leipzig | - | SC Motor Jena | 1:0 | ||||
| 4. Round | 25/08/1965 | BSG Chemie Leipzig | - | SC Motor Jena | 1:1 |  |
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| 5. Round | 11/09/1965 | SC Motor Jena | - | BSG Lokomotive Stendal | 3:0 | |
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| 7. Round | 03/11/1965 | SC Motor Jena | - | SC Dynamo Berlin | 2:0 | ||||
| 8. Round | 06/11/1965 | SC Empor Rostock | - | SC Motor Jena | 0:1 | ||||
| 9. Round | 13/11/1965 | SC Motor Jena | - | Dynamo Dresden | 0:0 | ||||
| 10. Round | 20/11/1965 | SC Turbine Erfurt | - | SC Motor Jena | 1:0 | ||||
| 14. Round | 12/02/1966 | FC Carl Zeiss Jena | - | FC Karl-Marx-Stadt | 3:0 | |
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| 16. Round | 26/02/1966 | FC Carl Zeiss Jena | - | 1. FC Lokomotive Leipzig | 2:4 | ||||
| 17. Round | 05/03/1966 | FC Carl Zeiss Jena | - | BSG Chemie Leipzig | 1:0 | ||||
| 19. Round | 19/03/1966 | FC Carl Zeiss Jena | - | BSG Wismut Aue | 2:1 | |
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| 20. Round | 02/04/1966 | BFC Dynamo | - | FC Carl Zeiss Jena | 2:2 | ||||
| 21. Round | 08/04/1966 | FC Carl Zeiss Jena | - | Hansa Rostock | 5:0 | ||||
| 23. Round | 16/04/1966 | FC Carl Zeiss Jena | - | Rot-Weiß Erfurt | 2:0 | ||||
| 24. Round | 04/05/1966 | BSG Motor Zwickau | - | FC Carl Zeiss Jena | 2:1 | ||||
| 25. Round | 07/05/1966 | FC Carl Zeiss Jena | - | 1. FC Magdeburg | 3:0 | |
Germany
GDR