| 1. Round | 17/08/1968 | 1. FC Köln | - | Kickers Offenbach | 2:1 | ||||
| 2. Round | 24/08/1968 | Kickers Offenbach | - | 1. FC Nürnberg | 2:1 |  |
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| 3. Round | 31/08/1968 | Kickers Offenbach | - | Alemannia Aachen | 1:1 | ||||
| 5. Round | 07/09/1968 | Kickers Offenbach | - | Hannover 96 | 1:1 | ||||
| 6. Round | 14/09/1968 | 1. FC Kaiserslautern | - | Kickers Offenbach | 2:1 | ||||
| 7. Round | 20/09/1968 | Kickers Offenbach | - | TSV 1860 München | 2:3 | ||||
| 8. Round | 28/09/1968 | Hamburger SV | - | Kickers Offenbach | 3:0 | ||||
| 10. Round | 19/10/1968 | Hertha BSC | - | Kickers Offenbach | 1:0 | ||||
| 12. Round | 30/10/1968 | MSV Duisburg | - | Kickers Offenbach | 2:1 | ||||
| 15. Round | 16/11/1968 | Kickers Offenbach | - | Bayern München | 0:0 | ||||
| 21. Round | 01/02/1969 | Kickers Offenbach | - | Bor. Mönchengladbach | 1:0 | ||||
| 30. Round | 12/04/1969 | Eintracht Braunschweig | - | Kickers Offenbach | 2:2 | ||||
| 31. Round | 17/05/1969 | Kickers Offenbach | - | VfB Stuttgart | 2:1 | ||||
| 34. Round | 07/06/1969 | Borussia Dortmund | - | Kickers Offenbach | 3:0 |
Germany