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 | ||||
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 | ||||
9. Round | 25/09/1999 | FC Carl Zeiss Jena | - | 1. FC Union Berlin | 0:1 | ||||
10. Round | 02/10/1999 | Stahl Eisenhüttenstadt | - | FC Carl Zeiss Jena | 2:1 |