| 3. Ronde | 27.08.1999 | 1. FC Köln | - | Stuttgarter Kickers | 4:1 | ||||
| 4. Ronde | 12.09.1999 | Stuttgarter Kickers | - | Rot-Weiß Oberhausen | 2:2 | ||||
| 6. Ronde | 26.09.1999 | Stuttgarter Kickers | - | Energie Cottbus | 1:0 | ||||
| 8. Ronde | 17.10.1999 | TeBe Berlin | - | Stuttgarter Kickers | 2:0 |  |
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| 9. Ronde | 23.10.1999 | Stuttgarter Kickers | - | Bor. Mönchengladbach | 3:1 | ||||
| 11. Ronde | 07.11.1999 | Stuttgarter Kickers | - | Kickers Offenbach | 2:1 | ||||
| 12. Ronde | 19.11.1999 | Fortuna Köln | - | Stuttgarter Kickers | 1:1 |  |
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| 13. Ronde | 26.11.1999 | Stuttgarter Kickers | - | 1. FSV Mainz 05 | 3:4 | ||||
| 14. Ronde | 05.12.1999 | 1. FC Nürnberg | - | Stuttgarter Kickers | 3:2 | |
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| 15. Ronde | 10.12.1999 | Stuttgarter Kickers | - | Chemnitzer FC | 2:2 |
Duitsland