| 4. Round | 19/08/1998 | 1. FC Union Berlin | - | VfB Leipzig | 0:2 | ||||
| 5. Round | 22/08/1998 | VfB Leipzig | - | FC Carl Zeiss Jena | 1:0 | ||||
| 6. Round | 08/09/1998 | FSV Zwickau | - | VfB Leipzig | 3:2 | ||||
| 7. Round | 11/09/1998 | VfB Leipzig | - | SD Croatia Berlin | 3:1 | ||||
| 8. Round | 18/09/1998 | SV Babelsberg 03 | - | VfB Leipzig | 3:3 |  |
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| 9. Round | 26/09/1998 | FC Berlin | - | VfB Leipzig | 2:1 | ||||
| 11. Round | 18/10/1998 | Dresdner SC | - | VfB Leipzig | 0:2 | ||||
| 16. Round | 04/12/1998 | VfB Leipzig | - | Stahl Eisenhüttenstadt | 3:2 | ||||
| 17. Round | 13/12/1998 | Sachsen Leipzig | - | VfB Leipzig | 3:3 | ||||
| 31. Round | 23/04/1999 | Erzgebirge Aue | - | VfB Leipzig | 0:1 |
Germany