1. Round | 10/08/1999 | Hertha BSC II | - | FC Carl Zeiss Jena | 1:1 | ||||
2. Round | 15/08/1999 | 1. FC Union Berlin | - | Hertha BSC II | 1:0 | ||||
3. Round | 21/08/1999 | Hertha BSC II | - | Stahl Eisenhüttenstadt | 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 | ||||
8. Round | 19/09/1999 | 1. FC Magdeburg | - | Hertha BSC II | 3:0 | ||||
11. Round | 16/10/1999 | SV Babelsberg 03 | - | Hertha BSC II | 4:0 | ||||
15. Round | 21/11/1999 | VFC Plauen | - | Hertha BSC II | 5:0 |