| 14. Round | 03/12/1999 | Kickers Offenbach | - | Bor. Mönchengladbach | 1:1 |  |
|||
| 15. Round | 12/12/1999 | Kickers Offenbach | - | Waldhof Mannheim | 1:1 |  |
|||
| 16. Round | 15/12/1999 | Energie Cottbus | - | Kickers Offenbach | 5:0 | ||||
| 17. Round | 19/12/1999 | Kickers Offenbach | - | Fortuna Köln | 4:3 | |
|||
| 18. Round | 12/02/2000 | Kickers Offenbach | - | 1. FSV Mainz 05 | 2:2 | |
|
||
| 19. Round | 18/02/2000 | 1. FC Nürnberg | - | Kickers Offenbach | 1:1 | ||||
| 20. Round | 25/02/2000 | Kickers Offenbach | - | Chemnitzer FC | 2:0 | |
|
||
| 21. Round | 05/03/2000 | Hannover 96 | - | Kickers Offenbach | 1:1 | |
|||
| 22. Round | 11/03/2000 | Kickers Offenbach | - | Karlsruher SC | 1:0 | ||||
| 23. Round | 19/03/2000 | Alemannia Aachen | - | Kickers Offenbach | 2:1 | |
|||
| 24. Round | 24/03/2000 | Kickers Offenbach | - | FC St. Pauli | 0:1 | |
|||
| 26. Round | 09/04/2000 | Kickers Offenbach | - | Rot-Weiß Oberhausen | 2:1 | ||||
| 27. Round | 16/04/2000 | SpVgg Greuther Fürth | - | Kickers Offenbach | 1:1 | ||||
| 30. Round | 07/05/2000 | Kickers Offenbach | - | TeBe Berlin | 2:1 | ||||
| 32. Round | 18/05/2000 | Waldhof Mannheim | - | Kickers Offenbach | 2:3 |
Romania