| 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 |  |
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| 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 |
Germany