| 3. Round | 20/08/1999 | 1. FC Magdeburg | - | VfB Leipzig | 0:1 | ||||
| 9. Round | 25/09/1999 | Sachsen Leipzig | - | VfB Leipzig | 2:0 | ||||
| 11. Round | 17/10/1999 | Lok Altmark Stendal | - | VfB Leipzig | 0:1 | ||||
| 12. Round | 22/10/1999 | VfB Leipzig | - | Erzgebirge Aue | 0:1 | ||||
| 15. Round | 20/11/1999 | Stahl Eisenhüttenstadt | - | VfB Leipzig | 1:2 |  |
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| 16. Round | 04/12/1999 | VfB Leipzig | - | BFC Dynamo | 3:0 | ||||
| 17. Round | 11/12/1999 | Dresdner SC | - | VfB Leipzig | 0:2 | |
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| 20. Round | 18/02/2000 | VfB Leipzig | - | 1. FC Magdeburg | 1:0 | ||||
| 19. Round | 22/03/2000 | TeBe Berlin II | - | VfB Leipzig | 3:1 | |
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| 26. Round | 02/04/2000 | VfB Leipzig | - | Sachsen Leipzig | 0:1 | ||||
| 27. Round | 11/04/2000 | VFC Plauen | - | VfB Leipzig | 2:1 | ||||
| 28. Round | 15/04/2000 | VfB Leipzig | - | Lok Altmark Stendal | 3:0 | ||||
| 24. Round | 19/04/2000 | VfB Leipzig | - | VfL Halle 96 | 1:0 | ||||
| 29. Round | 22/04/2000 | Erzgebirge Aue | - | VfB Leipzig | 2:0 | ||||
| 23. Round | 26/04/2000 | Hertha BSC II | - | VfB Leipzig | 0:2 | ||||
| 30. Round | 29/04/2000 | VfB Leipzig | - | FC Carl Zeiss Jena | 1:2 | ||||
| 33. Round | 13/05/2000 | BFC Dynamo | - | VfB Leipzig | 2:3 | ||||
| 34. Round | 20/05/2000 | VfB Leipzig | - | Dresdner SC | 4:0 | |
Slovakia