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 | ||||
8. Round | 18/09/1999 | 1. FC Union Berlin | - | Erzgebirge Aue | 1:1 |