1. Round | 11/08/1999 | 1. FC Magdeburg | - | BFC Dynamo | 1:1 | ||||
2. Round | 14/08/1999 | BFC Dynamo | - | FSV Zwickau | 6:1 | ||||
3. Round | 21/08/1999 | Rot-Weiß Erfurt | - | BFC Dynamo | 1:0 | ||||
4. Round | 24/08/1999 | BFC Dynamo | - | Hertha BSC II | 4:1 | ||||
5. Round | 28/08/1999 | VfL Halle 96 | - | BFC Dynamo | 0:0 | ||||
6. Round | 07/09/1999 | BFC Dynamo | - | Dynamo Dresden | 1:0 | ||||
7. Round | 12/09/1999 | Sachsen Leipzig | - | BFC Dynamo | 2:1 | ||||
8. Round | 18/09/1999 | BFC Dynamo | - | VFC Plauen | 1:0 | ||||
9. Round | 25/09/1999 | Lok Altmark Stendal | - | BFC Dynamo | 5:3 | ||||
10. Round | 02/10/1999 | BFC Dynamo | - | Erzgebirge Aue | 0:1 | ||||
11. Round | 17/10/1999 | FC Carl Zeiss Jena | - | BFC Dynamo | 1:1 | ||||
12. Round | 23/10/1999 | BFC Dynamo | - | 1. FC Union Berlin | 0:3 | ||||
13. Round | 06/11/1999 | Stahl Eisenhüttenstadt | - | BFC Dynamo | 1:0 | ||||
15. Round | 20/11/1999 | Dresdner SC | - | BFC Dynamo | 2:1 | ||||
28. Round | 15/04/2000 | BFC Dynamo | - | FC Carl Zeiss Jena | 0:2 | ||||
29. Round | 22/04/2000 | 1. FC Union Berlin | - | BFC Dynamo | 2:1 |