| 9. Round | 18/09/1999 | 1. FC Schweinfurt 05 | - | VfB Stuttgart II | 2:3 | ||||
| 10. Round | 26/09/1999 | VfB Stuttgart II | - | VfR Aalen | 5:2 | ||||
| 11. Round | 02/10/1999 | SV Wehen-Taunusstein | - | VfB Stuttgart II | 3:3 | ||||
| 21. Round | 04/03/2000 | Wacker Burghausen | - | VfB Stuttgart II | 1:1 | ||||
| 24. Round | 26/03/2000 | VfB Stuttgart II | - | FC Augsburg | 0:0 | ||||
| 25. Round | 01/04/2000 | Borussia Fulda | - | VfB Stuttgart II | 2:1 | ||||
| 26. Round | 09/04/2000 | VfB Stuttgart II | - | 1. FC Schweinfurt 05 | 1:0 | ||||
| 27. Round | 14/04/2000 | VfR Aalen | - | VfB Stuttgart II | 0:3 | ||||
| 28. Round | 23/04/2000 | VfB Stuttgart II | - | SV Wehen-Taunusstein | 3:1 | ||||
| 29. Round | 28/04/2000 | SV Lohhof | - | VfB Stuttgart II | 0:0 | ||||
| 30. Round | 06/05/2000 | VfB Stuttgart II | - | TSF Ditzingen | 2:0 | ||||
| 31. Round | 14/05/2000 | Bayern München II | - | VfB Stuttgart II | 1:6 | ||||
| 32. Round | 17/05/2000 | SSV Reutlingen | - | VfB Stuttgart II | 2:0 | ||||
| 33. Round | 21/05/2000 | VfB Stuttgart II | - | VfR Mannheim | 0:0 | ||||
| 34. Round | 27/05/2000 | FSV Frankfurt | - | VfB Stuttgart II | 0:2 dec. |
Germany