1. Round | 11/08/1999 | Sachsen Leipzig | - | VFC Plauen | 2:1 | ||||
2. Round | 14/08/1999 | VFC Plauen | - | SV Babelsberg 03 | 2:2 | ||||
3. Round | 22/08/1999 | VFC Plauen | - | Lok Altmark Stendal | 2:1 | ||||
4. Round | 25/08/1999 | Erzgebirge Aue | - | VFC Plauen | 3:0 | ||||
5. Round | 29/08/1999 | VFC Plauen | - | FC Carl Zeiss Jena | 1:1 | ||||
7. Round | 10/09/1999 | VFC Plauen | - | Stahl Eisenhüttenstadt | 2:5 | ||||
14. Round | 13/11/1999 | Rot-Weiß Erfurt | - | VFC Plauen | 1:0 | ||||
15. Round | 21/11/1999 | VFC Plauen | - | Hertha BSC II | 5:0 |