| 1. Round | 04/09/1949 | Holstein Kiel | - | Hamburger SV | 1:2 | ||||
| 1. Round | 11/09/1949 | Bremer SV | - | Holstein Kiel | 0:1 | ||||
| 1. Round | 25/09/1949 | Holstein Kiel | - | Harburger TB | 2:0 | ||||
| 2. Round | 02/10/1949 | Concordia Hamburg | - | Holstein Kiel | 1:0 | ||||
| 2. Round | 09/10/1949 | VfL Osnabrück | - | Holstein Kiel | 3:2 | ||||
| 2. Round | 16/10/1949 | Holstein Kiel | - | TuS Bremerhaven 93 | 6:1 | ||||
| 2. Round | 23/10/1949 | FC St. Pauli | - | Holstein Kiel | 2:1 | ||||
| 2. Round | 30/10/1949 | Holstein Kiel | - | Eimsbütteler TV | 0:1 | ||||
| 3. Round | 06/11/1949 | Holstein Kiel | - | Arminia Hannover | 1:1 | ||||
| 3. Round | 16/11/1949 | Holstein Kiel | - | Werder Bremen | 1:0 | ||||
| 4. Round | 25/12/1949 | Holstein Kiel | - | VfB Oldenburg | 7:4 | ||||
| 5. Round | 08/01/1950 | Holstein Kiel | - | Eintracht Braunschweig | 1:4 | ||||
| 5. Round | 15/01/1950 | SC Göttingen 05 | - | Holstein Kiel | 2:4 | ||||
| 5. Round | 22/01/1950 | Hannover 96 | - | Holstein Kiel | 0:0 | ||||
| 5. Round | 29/01/1950 | Holstein Kiel | - | VfL Osnabrück | 1:3 | ||||
| 6. Round | 05/02/1950 | TuS Bremerhaven 93 | - | Holstein Kiel | 3:1 | ||||
| 6. Round | 12/02/1950 | Holstein Kiel | - | Concordia Hamburg | 1:1 | ||||
| 6. Round | 19/02/1950 | Holstein Kiel | - | VfB Lübeck | 3:2 |
Germany