1. Round | 07/08/1999 | Dynamo Dresden | - | Lok Altmark Stendal | 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 | ||||
7. Round | 11/09/1999 | Dynamo Dresden | - | Dresdner SC | 2:2 | ||||
9. Round | 25/09/1999 | Dynamo Dresden | - | TeBe Berlin II | 1:1 |