| 1. Round | 11/08/2000 | Stuttgarter Kickers | - | Rot-Weiß Oberhausen | 1:0 |  |
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| 2. Round | 20/08/2000 | 1. FSV Mainz 05 | - | Stuttgarter Kickers | 2:2 | |
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| 3. Round | 06/09/2000 | Stuttgarter Kickers | - | Alemannia Aachen | 0:3 | ||||
| 4. Round | 10/09/2000 | FC St. Pauli | - | Stuttgarter Kickers | 4:0 | ||||
| 6. Round | 24/09/2000 | LR Ahlen | - | Stuttgarter Kickers | 1:1 | ||||
| 7. Round | 30/09/2000 | Stuttgarter Kickers | - | Waldhof Mannheim | 2:2 | ||||
| 8. Round | 15/10/2000 | SSV Reutlingen | - | Stuttgarter Kickers | 1:0 | ||||
| 11. Round | 03/11/2000 | Arminia Bielefeld | - | Stuttgarter Kickers | 0:0 | ||||
| 12. Round | 12/11/2000 | Stuttgarter Kickers | - | Bor. Mönchengladbach | 1:1 | ||||
| 13. Round | 19/11/2000 | SpVgg Greuther Fürth | - | Stuttgarter Kickers | 2:0 |
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