1. Round | 11/08/1999 | VfL Halle 96 | - | Erzgebirge Aue | 1:3 | ||||
2. Round | 15/08/1999 | FC Carl Zeiss Jena | - | VfL Halle 96 | 1:1 | ||||
3. Round | 21/08/1999 | VfL Halle 96 | - | 1. FC Union Berlin | 1:1 | ||||
4. Round | 24/08/1999 | Stahl Eisenhüttenstadt | - | VfL Halle 96 | 1:2 | ||||
5. Round | 28/08/1999 | VfL Halle 96 | - | BFC Dynamo | 0:0 | ||||
6. Round | 07/09/1999 | Dresdner SC | - | VfL Halle 96 | 3:0 | ||||
7. Round | 11/09/1999 | VfL Halle 96 | - | VfB Leipzig | 2:1 | ||||
8. Round | 19/09/1999 | TeBe Berlin II | - | VfL Halle 96 | 1:1 | ||||
9. Round | 25/09/1999 | VfL Halle 96 | - | 1. FC Magdeburg | 2:2 | ||||
10. Round | 02/10/1999 | FSV Zwickau | - | VfL Halle 96 | 0:1 | ||||
11. Round | 16/10/1999 | VfL Halle 96 | - | Rot-Weiß Erfurt | 4:3 | ||||
12. Round | 24/10/1999 | Hertha BSC II | - | VfL Halle 96 | 0:1 | ||||
13. Round | 06/11/1999 | SV Babelsberg 03 | - | VfL Halle 96 | 9:1 | ||||
14. Round | 13/11/1999 | VfL Halle 96 | - | Dynamo Dresden | 1:3 | ||||
15. Round | 20/11/1999 | Sachsen Leipzig | - | VfL Halle 96 | 1:0 | ||||
21. Round | 06/04/2000 | VfL Halle 96 | - | Stahl Eisenhüttenstadt | 1:1 | ||||
27. Round | 11/04/2000 | VfL Halle 96 | - | FSV Zwickau | 4:2 | ||||
28. Round | 15/04/2000 | Rot-Weiß Erfurt | - | VfL Halle 96 | 1:0 |