| 2. Round | 30/07/1988 | SV Darmstadt 98 | - | Kickers Offenbach | 3:0 | ||||
| 4. Round | 20/08/1988 | 1. FC Saarbrücken | - | Kickers Offenbach | 2:2 | ||||
| 5. Round | 27/08/1988 | Kickers Offenbach | - | Hertha BSC | 4:1 | ||||
| 6. Round | 03/09/1988 | Fortuna Köln | - | Kickers Offenbach | 3:0 | ||||
| 7. Round | 10/09/1988 | Kickers Offenbach | - | SG Union Solingen | 2:0 | ||||
| 8. Round | 14/09/1988 | 1. FSV Mainz 05 | - | Kickers Offenbach | 3:1 | ||||
| 9. Round | 17/09/1988 | Kickers Offenbach | - | SpVgg Bayreuth | 1:2 | ||||
| 13. Round | 22/10/1988 | SV Meppen | - | Kickers Offenbach | 4:0 | ||||
| 16. Round | 12/11/1988 | Kickers Offenbach | - | Fortuna Düsseldorf | 3:0 | ||||
| 17. Round | 19/11/1988 | Alemannia Aachen | - | Kickers Offenbach | 1:2 | ||||
| 18. Round | 26/11/1988 | Kickers Offenbach | - | Eintracht Braunschweig | 0:0 | ||||
| 19. Round | 11/02/1989 | Rot-Weiss Essen | - | Kickers Offenbach | 2:0 | ||||
| 20. Round | 18/02/1989 | Viktoria Aschaffenburg | - | Kickers Offenbach | 2:1 |
Germany