| 1. Round | 04/09/1949 | Harburger TB | - | Hannover 96 | 0:0 | ||||
| 1. Round | 11/09/1949 | Hamburger SV | - | Harburger TB | 3:2 | ||||
| 1. Round | 25/09/1949 | Holstein Kiel | - | Harburger TB | 2:0 | ||||
| 2. Round | 02/10/1949 | Eimsbütteler TV | - | Harburger TB | 2:0 | ||||
| 2. Round | 09/10/1949 | Harburger TB | - | FC St. Pauli | 2:3 | ||||
| 2. Round | 23/10/1949 | Harburger TB | - | Concordia Hamburg | 3:4 | ||||
| 2. Round | 30/10/1949 | Werder Bremen | - | Harburger TB | 4:2 | ||||
| 3. Round | 06/11/1949 | VfB Oldenburg | - | Harburger TB | 2:0 | ||||
| 3. Round | 13/11/1949 | TuS Bremerhaven 93 | - | Harburger TB | 3:1 | ||||
| 3. Round | 16/11/1949 | Harburger TB | - | VfB Lübeck | 2:0 | ||||
| 3. Round | 27/11/1949 | Eintracht Braunschweig | - | Harburger TB | 4:1 | ||||
| 4. Round | 11/12/1949 | Harburger TB | - | SC Göttingen 05 | 3:2 | ||||
| 4. Round | 26/12/1949 | Arminia Hannover | - | Harburger TB | 2:0 | ||||
| 5. Round | 01/01/1950 | Harburger TB | - | VfL Osnabrück | 1:5 | ||||
| 5. Round | 15/01/1950 | Harburger TB | - | Werder Bremen | 1:7 |
Germany