3. Round | 21/08/1999 | FSV Zwickau | - | Dresdner SC | 0:2 | ||||
4. Round | 25/08/1999 | Dresdner SC | - | Rot-Weiß Erfurt | 2:0 | ||||
5. Round | 28/08/1999 | Hertha BSC II | - | Dresdner SC | 1:1 | ||||
9. Round | 26/09/1999 | VFC Plauen | - | Dresdner SC | 3:1 | ||||
10. Round | 02/10/1999 | Dresdner SC | - | Lok Altmark Stendal | 2:0 | ||||
11. Round | 16/10/1999 | Erzgebirge Aue | - | Dresdner SC | 4:0 | ||||
12. Round | 23/10/1999 | Dresdner SC | - | FC Carl Zeiss Jena | 2:1 | ||||
13. Round | 06/11/1999 | 1. FC Union Berlin | - | Dresdner SC | 1:0 |