7. Round | 11/09/1999 | Erzgebirge Aue | - | FC Carl Zeiss Jena | 1:2 | ||||
10. Round | 02/10/1999 | Stahl Eisenhüttenstadt | - | FC Carl Zeiss Jena | 2:1 | ||||
11. Round | 17/10/1999 | FC Carl Zeiss Jena | - | BFC Dynamo | 1:1 | ||||
12. Round | 23/10/1999 | Dresdner SC | - | FC Carl Zeiss Jena | 2:1 | ||||
13. Round | 05/11/1999 | FC Carl Zeiss Jena | - | VfB Leipzig | 2:2 | ||||
14. Round | 13/11/1999 | TeBe Berlin II | - | FC Carl Zeiss Jena | 3:1 | ||||
16. Round | 04/12/1999 | FSV Zwickau | - | FC Carl Zeiss Jena | 0:2 |