| 1. Round | 17/08/2008 | Hamburger SV II | - | VFC Plauen | 1:1 | ||||
| 7. Round | 15/10/2008 | Hamburger SV II | - | Altona 93 | 2:2 | ||||
| 13. Round | 16/11/2008 | Hamburger SV II | - | SV Babelsberg 03 | 0:0 | ||||
| 16. Round | 09/12/2008 | Hamburger SV II | - | Hertha BSC II | 1:1 | ||||
| 31. Round | 17/05/2009 | Hamburger SV II | - | Hallescher FC | 1:1 | ||||
| 32. Round | 24/05/2009 | Hamburger SV II | - | Hansa Rostock II | 3:0 | ||||
| 33. Round | 30/05/2009 | Hertha BSC II | - | Hamburger SV II | 0:2 | ||||
| 34. Round | 07/06/2009 | Hamburger SV II | - | VfL Wolfsburg II | 2:1 |
Germany