| 1. Jornada | 10.08.1999 | Hertha II | - | FC Carl Zeiss Jena | 1:1 | ||||
| 2. Jornada | 15.08.1999 | FC Carl Zeiss Jena | - | VfL Halle 96 | 1:1 |  |
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| 5. Jornada | 29.08.1999 | VFC Plauen | - | FC Carl Zeiss Jena | 1:1 | ||||
| 6. Jornada | 07.09.1999 | FC Carl Zeiss Jena | - | Lok Altmark Stendal | 2:1 |  |
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| 7. Jornada | 11.09.1999 | Erzgebirge Aue | - | FC Carl Zeiss Jena | 1:2 | ||||
| 8. Jornada | 18.09.1999 | FC Carl Zeiss Jena | - | SV Babelsberg 03 | 1:2 | |
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| 9. Jornada | 25.09.1999 | FC Carl Zeiss Jena | - | 1. FC Union Berlin | 0:1 | ||||
| 10. Jornada | 02.10.1999 | Stahl Eisenhüttenstadt | - | FC Carl Zeiss Jena | 2:1 |
Alemania