| 1. Round | 25/07/2008 | Rot-Weiß Erfurt | - | Dynamo Dresden | 0:1 | ||||
| 2. Round | 13/08/2008 | Dynamo Dresden | - | Kickers Emden | 1:2 | ||||
| 3. Round | 16/08/2008 | Bayern München II | - | Dynamo Dresden | 1:0 |  |
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| 4. Round | 23/08/2008 | Dynamo Dresden | - | VfB Stuttgart II | 1:0 | ||||
| 5. Round | 30/08/2008 | Kickers Offenbach | - | Dynamo Dresden | 2:2 | ||||
| 7. Round | 21/09/2008 | Wuppertaler SV | - | Dynamo Dresden | 1:0 | ||||
| 9. Round | 05/10/2008 | Dynamo Dresden | - | Eintracht Braunschweig | 1:1 | ||||
| 17. Round | 30/11/2008 | Dynamo Dresden | - | SV Sandhausen | 1:1 | ||||
| 18. Round | 06/12/2008 | Jahn Regensburg | - | Dynamo Dresden | 1:0 | ||||
| 20. Round | 20/12/2008 | Dynamo Dresden | - | Rot-Weiß Erfurt | 1:1 | |
Germany