| 1. Round | 11/08/1999 | VfL Halle 96 | - | Erzgebirge Aue | 1:3 | ||||
| 2. Round | 14/08/1999 | Erzgebirge Aue | - | Dynamo Dresden | 1:1 | ||||
| 3. Round | 21/08/1999 | Sachsen Leipzig | - | Erzgebirge Aue | 4:0 | ||||
| 4. Round | 25/08/1999 | Erzgebirge Aue | - | VFC Plauen | 3:0 |  |
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| 5. Round | 29/08/1999 | Lok Altmark Stendal | - | Erzgebirge Aue | 2:1 | ||||
| 7. Round | 11/09/1999 | Erzgebirge Aue | - | FC Carl Zeiss Jena | 1:2 | ||||
| 8. Round | 18/09/1999 | 1. FC Union Berlin | - | Erzgebirge Aue | 1:1 |
Germany