| 2. Round | 08/08/1999 | VfB Stuttgart II | - | SC Pfullendorf | 1:1 | ||||
| 4. Round | 22/08/1999 | VfB Stuttgart II | - | Wacker Burghausen | 1:0 | ||||
| 6. Round | 31/08/1999 | VfB Stuttgart II | - | TSV 1860 München II | 1:1 | ||||
| 8. Round | 12/09/1999 | VfB Stuttgart II | - | Borussia Fulda | 2:2 |  |
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| 9. Round | 18/09/1999 | 1. FC Schweinfurt 05 | - | VfB Stuttgart II | 2:3 | ||||
| 14. Round | 24/10/1999 | VfB Stuttgart II | - | Bayern München II | 3:0 | ||||
| 17. Round | 13/11/1999 | VfB Stuttgart II | - | FSV Frankfurt | 0:0 | ||||
| 30. Round | 06/05/2000 | VfB Stuttgart II | - | TSF Ditzingen | 2:0 |
Germany