| 1. Round | 01/08/1998 | VfB Stuttgart II | - | SSV Reutlingen | 0:2 | ||||
| 23. Round | 21/03/1999 | VfB Stuttgart II | - | SC Pfullendorf | 1:0 |  |
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| 24. Round | 27/03/1999 | VfB Stuttgart II | - | FC Augsburg | 1:3 | |
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| 26. Round | 11/04/1999 | VfB Stuttgart II | - | TSV 1860 München II | 4:1 |  |
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| 28. Round | 24/04/1999 | VfB Stuttgart II | - | FSV Frankfurt | 1:2 |  |
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| 29. Round | 30/04/1999 | SC Weismain | - | VfB Stuttgart II | 0:0 | ||||
| 30. Round | 08/05/1999 | VfB Stuttgart II | - | VfR Mannheim | 0:2 | ||||
| 32. Round | 16/05/1999 | VfB Stuttgart II | - | TSF Ditzingen | 2:0 | |
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| 34. Round | 28/05/1999 | VfB Stuttgart II | - | Bayern München II | 2:2 |
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