| 3. Round | 31/08/2008 | Hamburger SV II | - | VfB Lübeck | 2:1 | ||||
| 4. Round | 13/09/2008 | SV Wilhelmshaven | - | Hamburger SV II | 0:4 | ||||
| 5. Round | 21/09/2008 | Hamburger SV II | - | 1. FC Magdeburg | 0:1 | ||||
| 11. Round | 01/11/2008 | Hamburger SV II | - | Hannover 96 II | 0:3 | ||||
| 12. Round | 08/11/2008 | Holstein Kiel | - | Hamburger SV II | 2:1 | ||||
| 15. Round | 29/11/2008 | Hansa Rostock II | - | Hamburger SV II | 3:0 | ||||
| 17. Round | 16/12/2008 | VfL Wolfsburg II | - | Hamburger SV II | 2:0 |
Germany