| 1. Round | 30/07/1999 | SC Pfullendorf | - | SSV Reutlingen | 1:1 | ||||
| 2. Round | 11/08/1999 | SSV Reutlingen | - | SV Darmstadt 98 | 2:1 |  |
|||
| 3. Round | 14/08/1999 | Wacker Burghausen | - | SSV Reutlingen | 0:1 | |
 |
||
| 4. Round | 21/08/1999 | SSV Reutlingen | - | Karlsruher SC II | 4:1 | |
|
||
| 5. Round | 28/08/1999 | TSV 1860 München II | - | SSV Reutlingen | 0:2 | ||||
| 6. Round | 31/08/1999 | SSV Reutlingen | - | FC Augsburg | 2:1 | ||||
| 7. Round | 03/09/1999 | Borussia Fulda | - | SSV Reutlingen | 0:1 | ||||
| 8. Round | 11/09/1999 | SSV Reutlingen | - | 1. FC Schweinfurt 05 | 4:0 | |
|||
| 9. Round | 18/09/1999 | VfR Aalen | - | SSV Reutlingen | 1:2 | ||||
| 10. Round | 25/09/1999 | SSV Reutlingen | - | SV Wehen-Taunusstein | 3:1 | |
|||
| 13. Round | 17/10/1999 | Bayern München II | - | SSV Reutlingen | 0:3 | ||||
| 14. Round | 24/10/1999 | SSV Reutlingen | - | VfR Mannheim | 5:1 | |
|||
| 15. Round | 30/10/1999 | VfB Stuttgart II | - | SSV Reutlingen | 0:2 |
Germany