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 | ||||
20. Round | 20/02/2000 | 1. FC Union Berlin | - | VfL Halle 96 | 2:2 |