| 5. Round | 17/09/1999 | Rot-Weiß Oberhausen | - | VfL Bochum | 3:0 | ||||
| 6. Round | 24/09/1999 | VfL Bochum | - | SpVgg Greuther Fürth | 1:2 | ||||
| 7. Round | 03/10/1999 | Stuttgarter Kickers | - | VfL Bochum | 0:0 |  |
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| 8. Round | 16/10/1999 | VfL Bochum | - | Energie Cottbus | 2:4 | ||||
| 9. Round | 24/10/1999 | VfL Bochum | - | TeBe Berlin | 2:6 | ||||
| 10. Round | 01/11/1999 | Bor. Mönchengladbach | - | VfL Bochum | 0:1 | ||||
| 11. Round | 05/11/1999 | VfL Bochum | - | Waldhof Mannheim | 2:0 | ||||
| 12. Round | 19/11/1999 | Kickers Offenbach | - | VfL Bochum | 2:1 | ||||
| 13. Round | 27/11/1999 | VfL Bochum | - | Fortuna Köln | 3:0 | ||||
| 14. Round | 05/12/1999 | 1. FSV Mainz 05 | - | VfL Bochum | 0:1 | ||||
| 15. Round | 11/12/1999 | VfL Bochum | - | 1. FC Nürnberg | 2:1 | ||||
| 16. Round | 14/12/1999 | Chemnitzer FC | - | VfL Bochum | 3:3 | ||||
| 17. Round | 09/02/2000 | VfL Bochum | - | Hannover 96 | 2:1 | ||||
| 18. Round | 14/02/2000 | VfL Bochum | - | Karlsruher SC | 2:1 | ||||
| 19. Round | 20/02/2000 | Alemannia Aachen | - | VfL Bochum | 0:1 | ||||
| 20. Round | 25/02/2000 | VfL Bochum | - | FC St. Pauli | 2:0 | ||||
| 21. Round | 03/03/2000 | 1. FC Köln | - | VfL Bochum | 3:0 | ||||
| 24. Round | 25/03/2000 | VfL Bochum | - | Stuttgarter Kickers | 2:1 |
Germany