1. Round | 13/08/1999 | 1. FSV Mainz 05 | - | Kickers Offenbach | 1:1 | ||||
2. Round | 23/08/1999 | Kickers Offenbach | - | 1. FC Nürnberg | 1:3 | ||||
3. Round | 27/08/1999 | Chemnitzer FC | - | Kickers Offenbach | 3:0 | ||||
5. Round | 17/09/1999 | Karlsruher SC | - | Kickers Offenbach | 1:1 | ||||
6. Round | 26/09/1999 | Kickers Offenbach | - | Alemannia Aachen | 1:2 | ||||
7. Round | 01/10/1999 | FC St. Pauli | - | Kickers Offenbach | 1:1 | ||||
8. Round | 15/10/1999 | Kickers Offenbach | - | 1. FC Köln | 0:1 |