| 1. Jornada | 15.08.1999 | Alemannia Aachen | - | Stuttgarter Kickers | 4:1 | ||||
| 2. Jornada | 22.08.1999 | Stuttgarter Kickers | - | FC St. Pauli | 2:1 | ||||
| 9. Jornada | 23.10.1999 | Stuttgarter Kickers | - | Bor. Mönchengladbach | 3:1 | ||||
| 10. Jornada | 29.10.1999 | Waldhof Mannheim | - | Stuttgarter Kickers | 4:3 | ||||
| 14. Jornada | 05.12.1999 | 1. FC Nürnberg | - | Stuttgarter Kickers | 3:2 | ||||
| 15. Jornada | 10.12.1999 | Stuttgarter Kickers | - | Chemnitzer FC | 2:2 | ||||
| 20. Jornada | 27.02.2000 | Stuttgarter Kickers | - | Colonia | 1:2 | ||||
| 17. Jornada | 02.03.2000 | Stuttgarter Kickers | - | Karlsruher SC | 2:1 | ||||
| 21. Jornada | 05.03.2000 | Rot-Weiß Oberhausen | - | Stuttgarter Kickers | 2:2 | ||||
| 22. Jornada | 12.03.2000 | Stuttgarter Kickers | - | SpVgg Greuther Fürth | 1:5 | ||||
| 23. Jornada | 19.03.2000 | Energie Cottbus | - | Stuttgarter Kickers | 1:0 | ||||
| 24. Jornada | 25.03.2000 | VfL Bochum | - | Stuttgarter Kickers | 2:1 |
Alemania