| 1. Ronde | 10.08.1999 | Hertha BSC II | - | FC Carl Zeiss Jena | 1:1 | ||||
| 2. Ronde | 15.08.1999 | FC Carl Zeiss Jena | - | VfL Halle 96 | 1:1 |  |
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| 3. Ronde | 20.08.1999 | Dynamo Dresden | - | FC Carl Zeiss Jena | 1:0 | ||||
| 4. Ronde | 25.08.1999 | FC Carl Zeiss Jena | - | Sachsen Leipzig | 0:0 | ||||
| 5. Ronde | 29.08.1999 | VFC Plauen | - | FC Carl Zeiss Jena | 1:1 | |
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| 8. Ronde | 18.09.1999 | FC Carl Zeiss Jena | - | SV Babelsberg 03 | 1:2 | ||||
| 14. Ronde | 13.11.1999 | TeBe Berlin II | - | FC Carl Zeiss Jena | 3:1 | ||||
| 16. Ronde | 04.12.1999 | FSV Zwickau | - | FC Carl Zeiss Jena | 0:2 |
Duitsland
Portugal