1. Round | 10/08/1999 | Hertha BSC II | - | FC Carl Zeiss Jena | 1:1 | ||||
2. Round | 15/08/1999 | FC Carl Zeiss Jena | - | VfL Halle 96 | 1:1 | ||||
3. Round | 20/08/1999 | Dynamo Dresden | - | FC Carl Zeiss Jena | 1:0 | ||||
4. Round | 25/08/1999 | FC Carl Zeiss Jena | - | Sachsen Leipzig | 0:0 | ||||
5. Round | 29/08/1999 | VFC Plauen | - | FC Carl Zeiss Jena | 1:1 | ||||
6. Round | 07/09/1999 | FC Carl Zeiss Jena | - | Lok Altmark Stendal | 2:1 | ||||
7. Round | 11/09/1999 | Erzgebirge Aue | - | FC Carl Zeiss Jena | 1:2 | ||||
8. Round | 18/09/1999 | FC Carl Zeiss Jena | - | SV Babelsberg 03 | 1:2 | ||||
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 | ||||
15. Round | 20/11/1999 | FC Carl Zeiss Jena | - | 1. FC Magdeburg | 3:2 | ||||
16. Round | 04/12/1999 | FSV Zwickau | - | FC Carl Zeiss Jena | 0:2 | ||||
17. Round | 10/12/1999 | FC Carl Zeiss Jena | - | Rot-Weiß Erfurt | 1:1 |