| 1. Round | 13/08/1999 | FC St. Pauli | - | SpVgg Greuther Fürth | 0:0 | ||||
| 2. Round | 20/08/1999 | SpVgg Greuther Fürth | - | 1. FC Köln | 0:0 |  |
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| 4. Round | 12/09/1999 | SpVgg Greuther Fürth | - | Energie Cottbus | 1:0 | ||||
| 5. Round | 19/09/1999 | SpVgg Greuther Fürth | - | Stuttgarter Kickers | 0:0 | |
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| 6. Round | 24/09/1999 | VfL Bochum | - | SpVgg Greuther Fürth | 1:2 | ||||
| 7. Round | 03/10/1999 | SpVgg Greuther Fürth | - | TeBe Berlin | 2:0 | ||||
| 8. Round | 15/10/1999 | Bor. Mönchengladbach | - | SpVgg Greuther Fürth | 2:0 | ||||
| 9. Round | 24/10/1999 | SpVgg Greuther Fürth | - | Waldhof Mannheim | 0:0 | ||||
| 10. Round | 31/10/1999 | Kickers Offenbach | - | SpVgg Greuther Fürth | 1:0 | ||||
| 14. Round | 03/12/1999 | Chemnitzer FC | - | SpVgg Greuther Fürth | 5:0 |
Bulgaria