5. Round | 29/08/1999 | VFC Plauen | - | FC Carl Zeiss Jena | 1:1 | ||||
6. Round | 07/09/1999 | 1. FC Union Berlin | - | VFC Plauen | 1:0 | ||||
7. Round | 10/09/1999 | VFC Plauen | - | Stahl Eisenhüttenstadt | 2:5 | ||||
8. Round | 18/09/1999 | BFC Dynamo | - | VFC Plauen | 1:0 | ||||
9. Round | 26/09/1999 | VFC Plauen | - | Dresdner SC | 3:1 | ||||
10. Round | 31/10/1999 | VfB Leipzig | - | VFC Plauen | 2:2 | ||||
16. Round | 04/12/1999 | VfL Halle 96 | - | VFC Plauen | 3:1 |