| 1. Round | 02/10/1949 | Kickers Offenbach | - | Stuttgarter Kickers | 3:0 | ||||
| 4. Round | 09/10/1949 | Kickers Offenbach | - | Waldhof Mannheim | 0:6 | ||||
| 7. Round | 30/10/1949 | Kickers Offenbach | - | TSV 1860 München | 4:1 | ||||
| 16. Round | 08/01/1950 | 1. FC Nürnberg | - | Kickers Offenbach | 3:0 | ||||
| 17. Round | 15/01/1950 | Kickers Offenbach | - | VfB Stuttgart | 4:1 | ||||
| 19. Round | 29/01/1950 | Stuttgarter Kickers | - | Kickers Offenbach | 1:1 | ||||
| 20. Round | 05/02/1950 | Waldhof Mannheim | - | Kickers Offenbach | 3:3 | ||||
| 21. Round | 12/02/1950 | Kickers Offenbach | - | SSV Jahn Regensburg | 4:0 | ||||
| 22. Round | 19/02/1950 | Kickers Offenbach | - | FSV Frankfurt | 2:1 | ||||
| 23. Round | 26/02/1950 | TSV Schwaben Augsburg | - | Kickers Offenbach | 2:3 | ||||
| 30. Round | 15/04/1950 | Kickers Offenbach | - | 1. FC Schweinfurt 05 | 2:1 | ||||
| 31. Round | 22/04/1950 | Kickers Offenbach | - | BC Augsburg | 3:0 | ||||
| 32. Round | 29/04/1950 | Frankfurter SG Eintracht | - | Kickers Offenbach | 1:2 | ||||
| 33. Round | 07/05/1950 | Kickers Offenbach | - | 1. FC Nürnberg | 2:0 | ||||
| 34. Round | 14/05/1950 | VfB Stuttgart | - | Kickers Offenbach | 1:2 |
Germany