| 1. Round | 16/08/2008 | Hamburger SV [Youth] | - | Hannover 96 [Youth] | 1:3 | ||||
| 2. Round | 24/08/2008 | Energie Cottbus [Youth] | - | Hamburger SV [Youth] | 1:4 | ||||
| 3. Round | 30/08/2008 | Hamburger SV [Youth] | - | VfL Osnabrück [Youth] | 3:2 |  |
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| 4. Round | 14/09/2008 | VfL Wolfsburg [Youth] | - | Hamburger SV [Youth] | 0:1 | ||||
| 5. Round | 27/09/2008 | Hamburger SV [Youth] | - | Eintracht Braunschweig [Youth] | 2:2 | |
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| 6. Round | 05/10/2008 | 1. FC Union Berlin [Youth] | - | Hamburger SV [Youth] | 0:2 | |
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| 7. Round | 26/10/2008 | Hamburger SV [Youth] | - | Hansa Rostock [Youth] | 4:1 | |
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| 8. Round | 02/11/2008 | Hertha BSC [Youth] | - | Hamburger SV [Youth] | 0:3 | |
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| 9. Round | 09/11/2008 | FC St. Pauli [Youth] | - | Hamburger SV [Youth] | 1:6 | |
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| 10. Round | 15/11/2008 | Hamburger SV [Youth] | - | FC Carl Zeiss Jena [Youth] | 2:0 | |
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| 11. Round | 29/11/2008 | Rot-Weiß Erfurt [Youth] | - | Hamburger SV [Youth] | 0:3 | |
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| 18. Round | 15/03/2009 | Eintracht Braunschweig [Youth] | - | Hamburger SV [Youth] | 3:2 | ||||
| 19. Round | 22/03/2009 | Hamburger SV [Youth] | - | 1. FC Union Berlin [Youth] | 2:0 |
Germany