1. Round | 11/08/1999 | SV Babelsberg 03 | - | VfB Leipzig | 3:1 | ||||
2. Round | 14/08/1999 | VfB Leipzig | - | TeBe Berlin II | 2:0 | ||||
3. Round | 20/08/1999 | 1. FC Magdeburg | - | VfB Leipzig | 0:1 | ||||
4. Round | 25/08/1999 | VfB Leipzig | - | FSV Zwickau | 0:0 | ||||
5. Round | 28/08/1999 | Rot-Weiß Erfurt | - | VfB Leipzig | 1:0 | ||||
6. Round | 07/09/1999 | VfB Leipzig | - | Hertha BSC II | 2:1 | ||||
7. Round | 11/09/1999 | VfL Halle 96 | - | VfB Leipzig | 2:1 | ||||
9. Round | 25/09/1999 | Sachsen Leipzig | - | VfB Leipzig | 2:0 | ||||
11. Round | 17/10/1999 | Lok Altmark Stendal | - | VfB Leipzig | 0:1 | ||||
8. Round | 17/10/1999 | VfB Leipzig | - | Dynamo Dresden | 0:2 dec. | ||||
12. Round | 22/10/1999 | VfB Leipzig | - | Erzgebirge Aue | 0:1 | ||||
13. Round | 05/11/1999 | FC Carl Zeiss Jena | - | VfB Leipzig | 2:2 | ||||
14. Round | 13/11/1999 | VfB Leipzig | - | 1. FC Union Berlin | 2:3 | ||||
15. Round | 20/11/1999 | Stahl Eisenhüttenstadt | - | VfB Leipzig | 1:2 |