| 1. Round | 13/08/2000 | SpVgg Greuther Fürth | - | Chemnitzer FC | 4:1 | ||||
| 3. Round | 05/09/2000 | Chemnitzer FC | - | 1. FC Saarbrücken | 1:3 | ||||
| 4. Round | 10/09/2000 | VfL Osnabrück | - | Chemnitzer FC | 1:1 |  |
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| 5. Round | 17/09/2000 | Chemnitzer FC | - | SSV Ulm 1846 | 1:0 | ||||
| 6. Round | 24/09/2000 | Rot-Weiß Oberhausen | - | Chemnitzer FC | 4:1 | ||||
| 7. Round | 01/10/2000 | Chemnitzer FC | - | 1. FSV Mainz 05 | 0:2 | ||||
| 8. Round | 13/10/2000 | Alemannia Aachen | - | Chemnitzer FC | 1:2 | ||||
| 9. Round | 20/10/2000 | Chemnitzer FC | - | FC St. Pauli | 1:3 | ||||
| 11. Round | 03/11/2000 | Chemnitzer FC | - | LR Ahlen | 2:2 |
Germany