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 | ||||
10. Round | 01/10/1999 | 1. FC Magdeburg | - | Dynamo Dresden | 1:2 | ||||
8. Round | 17/10/1999 | VfB Leipzig | - | Dynamo Dresden | 0:2 dec. | ||||
12. Round | 23/10/1999 | Rot-Weiß Erfurt | - | Dynamo Dresden | 2:1 | ||||
13. Round | 06/11/1999 | Dynamo Dresden | - | Hertha BSC II | 2:3 | ||||
16. Round | 04/12/1999 | Dynamo Dresden | - | Sachsen Leipzig | 0:1 |