| 2. Round | 06/08/1999 | 1. FC Schweinfurt 05 | - | VfR Mannheim | 3:2 | ||||
| 3. Round | 13/08/1999 | 1. FC Schweinfurt 05 | - | VfR Aalen | 1:2 | ||||
| 6. Round | 31/08/1999 | TSF Ditzingen | - | 1. FC Schweinfurt 05 | 0:2 | ||||
| 15. Round | 30/10/1999 | 1. FC Schweinfurt 05 | - | Karlsruher SC II | 1:2 | ||||
| 19. Round | 27/11/1999 | VfR Mannheim | - | 1. FC Schweinfurt 05 | 4:1 | ||||
| 20. Round | 04/12/1999 | VfR Aalen | - | 1. FC Schweinfurt 05 | 1:2 | ||||
| 25. Round | 01/04/2000 | 1. FC Schweinfurt 05 | - | SSV Reutlingen | 1:0 | ||||
| 28. Round | 22/04/2000 | Quelle Fürth | - | 1. FC Schweinfurt 05 | 1:0 | ||||
| 33. Round | 20/05/2000 | 1. FC Schweinfurt 05 | - | TSV 1860 München II | 1:0 | ||||
| 34. Round | 27/05/2000 | FC Augsburg | - | 1. FC Schweinfurt 05 | 2:4 |  |
Serbia