2. Round | 15/08/1999 | 1. FC Union Berlin | - | Hertha BSC II | 1:0 | ||||
4. Round | 24/08/1999 | BFC Dynamo | - | Hertha BSC II | 4:1 | ||||
5. Round | 28/08/1999 | Hertha BSC II | - | Dresdner SC | 1:1 | ||||
6. Round | 07/09/1999 | VfB Leipzig | - | Hertha BSC II | 2:1 | ||||
7. Round | 12/09/1999 | Hertha BSC II | - | TeBe Berlin II | 3:2 | ||||
8. Round | 19/09/1999 | 1. FC Magdeburg | - | Hertha BSC II | 3:0 | ||||
10. Round | 03/10/1999 | Rot-Weiß Erfurt | - | Hertha BSC II | 1:0 |