| 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 |  |
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| 4. Round | 24/08/1999 | BFC Dynamo | - | Hertha BSC II | 4:1 | ||||
| 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 | |
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| 9. Round | 24/09/1999 | Hertha BSC II | - | FSV Zwickau | 4:1 |  |
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| 13. Round | 06/11/1999 | Dynamo Dresden | - | Hertha BSC II | 2:3 | ||||
| 16. Round | 05/12/1999 | Hertha BSC II | - | Lok Altmark Stendal | 1:1 | ||||
| 17. Round | 11/12/1999 | Erzgebirge Aue | - | Hertha BSC II | 2:1 | |
Germany