1. Round | 07/08/1999 | Rot-Weiß Erfurt | - | 1. FC Union Berlin | 0:1 | ||||
2. Round | 15/08/1999 | 1. FC Union Berlin | - | Hertha BSC II | 1:0 | ||||
3. Round | 21/08/1999 | VfL Halle 96 | - | 1. FC Union Berlin | 1:1 | ||||
4. Round | 24/08/1999 | 1. FC Union Berlin | - | Dynamo Dresden | 1:1 | ||||
5. Round | 28/08/1999 | Sachsen Leipzig | - | 1. FC Union Berlin | 0:0 | ||||
6. Round | 07/09/1999 | 1. FC Union Berlin | - | VFC Plauen | 1:0 | ||||
7. Round | 11/09/1999 | Lok Altmark Stendal | - | 1. FC Union Berlin | 1:1 | ||||
8. Round | 18/09/1999 | 1. FC Union Berlin | - | Erzgebirge Aue | 1:1 | ||||
9. Round | 25/09/1999 | FC Carl Zeiss Jena | - | 1. FC Union Berlin | 0:1 | ||||
15. Round | 21/11/1999 | 1. FC Union Berlin | - | TeBe Berlin II | 1:2 | ||||
16. Round | 05/12/1999 | 1. FC Magdeburg | - | 1. FC Union Berlin | 1:2 | ||||
17. Round | 11/12/1999 | 1. FC Union Berlin | - | FSV Zwickau | 3:0 | ||||
23. Round | 11/03/2000 | VFC Plauen | - | 1. FC Union Berlin | 0:1 | ||||
25. Round | 25/03/2000 | Erzgebirge Aue | - | 1. FC Union Berlin | 2:1 |