| 1. Round | 31/07/1998 | TSV 1860 München II | - | Kickers Offenbach | 0:2 |  |
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| 2. Round | 08/08/1998 | Kickers Offenbach | - | Karlsruher SC II | 2:0 | ||||
| 23. Round | 20/03/1999 | SC Neukirchen | - | Kickers Offenbach | 1:3 | ||||
| 24. Round | 28/03/1999 | Kickers Offenbach | - | TSF Ditzingen | 5:0 | ||||
| 25. Round | 03/04/1999 | FC Augsburg | - | Kickers Offenbach | 1:1 | ||||
| 26. Round | 11/04/1999 | Bayern München II | - | Kickers Offenbach | 1:3 |  |
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| 27. Round | 18/04/1999 | Kickers Offenbach | - | SSV Reutlingen | 1:2 | ||||
| 28. Round | 24/04/1999 | SV Wehen-Taunusstein | - | Kickers Offenbach | 2:1 | ||||
| 29. Round | 30/04/1999 | Kickers Offenbach | - | Wacker Burghausen | 2:2 | ||||
| 30. Round | 08/05/1999 | 1. FC Schweinfurt 05 | - | Kickers Offenbach | 1:1 | ||||
| 31. Round | 13/05/1999 | Kickers Offenbach | - | Waldhof Mannheim | 0:0 | ||||
| 32. Round | 16/05/1999 | SC Pfullendorf | - | Kickers Offenbach | 1:2 | ||||
| 33. Round | 21/05/1999 | Kickers Offenbach | - | VfB Stuttgart II | 3:0 | ||||
| 34. Round | 28/05/1999 | Borussia Fulda | - | Kickers Offenbach | 0:2 |
Germany