1. Round | 31/07/1999 | VfL Hamm/Sieg | - | Stuttgarter Kickers | 0:4 | ||||
2. Round | 07/08/1999 | VFC Plauen | - | Stuttgarter Kickers | 1:2 | ||||
3. Round | 12/10/1999 | Stuttgarter Kickers | - | Borussia Dortmund | 3:1 | ||||
Round of 16 | 01/12/1999 | Stuttgarter Kickers | - | Arminia Bielefeld | 3:2 aet | ||||
Quarter-finals | 22/12/1999 | Stuttgarter Kickers | - | SC Freiburg | 1:0 |