1. Round | 07/08/1999 | Dynamo Dresden | - | Lok Altmark Stendal | 1:1 | ||||
2. Round | 14/08/1999 | Erzgebirge Aue | - | Dynamo Dresden | 1:1 | ||||
3. Round | 20/08/1999 | Dynamo Dresden | - | FC Carl Zeiss Jena | 1:0 | ||||
4. Round | 24/08/1999 | 1. FC Union Berlin | - | Dynamo Dresden | 1:1 | ||||
5. Round | 27/08/1999 | Dynamo Dresden | - | Stahl Eisenhüttenstadt | 1:1 | ||||
6. Round | 07/09/1999 | BFC Dynamo | - | Dynamo Dresden | 1:0 | ||||
13. Round | 06/11/1999 | Dynamo Dresden | - | Hertha BSC II | 2:3 |