| 1. Round | 31/07/1999 | VfL Hamm/Sieg | - | Stuttgarter Kickers | 0:4 |  |
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| 2. Round | 07/08/1999 | VFC Plauen | - | Stuttgarter Kickers | 1:2 | ||||
| Round of 16 | 01/12/1999 | Stuttgarter Kickers | - | Arminia Bielefeld | 3:2 aet | |
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| Quarter-finals | 22/12/1999 | Stuttgarter Kickers | - | SC Freiburg | 1:0 | |
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| Semi-finals | 15/02/2000 | Werder Bremen | - | Stuttgarter Kickers | 2:1 aet | |
Germany