| 1. Round | 01/08/1998 | VfB Leipzig | - | Dynamo Dresden | 2:0 |  |
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| 2. Round | 09/08/1998 | Chemnitzer FC | - | VfB Leipzig | 4:3 |  |
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| 3. Round | 14/08/1998 | VfB Leipzig | - | 1. FC Magdeburg | 1:1 | |
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| 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 | |
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| 7. Round | 11/09/1998 | VfB Leipzig | - | SD Croatia Berlin | 3:1 | ||||
| 8. Round | 18/09/1998 | SV Babelsberg 03 | - | VfB Leipzig | 3:3 | ||||
| 17. Round | 13/12/1998 | Sachsen Leipzig | - | VfB Leipzig | 3:3 | ||||
| 21. Round | 13/02/1999 | VfB Leipzig | - | 1. FC Union Berlin | 1:0 | ||||
| 24. Round | 06/03/1999 | SD Croatia Berlin | - | VfB Leipzig | 0:2 | ||||
| 22. Round | 16/03/1999 | FC Carl Zeiss Jena | - | VfB Leipzig | 1:0 |
Slovakia