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 | ||||
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 | ||||
10. Round | 31/10/1999 | VfB Leipzig | - | VFC Plauen | 2:2 | ||||
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 | ||||
16. Round | 04/12/1999 | VfB Leipzig | - | BFC Dynamo | 3:0 | ||||
17. Round | 11/12/1999 | Dresdner SC | - | VfB Leipzig | 0:2 |