1. Round | 09/08/2008 | Huddersfield Town | - | Stockport County | 1:1 | ||||
2. Round | 16/08/2008 | Stockport County | - | Leicester City | 0:0 | ||||
3. Round | 23/08/2008 | Hartlepool United | - | Stockport County | 0:1 | ||||
4. Round | 30/08/2008 | Stockport County | - | Scunthorpe United | 0:3 | ||||
6. Round | 13/09/2008 | Leyton Orient | - | Stockport County | 0:3 | ||||
5. Round | 16/09/2008 | Stockport County | - | Northampton Town | 1:1 | ||||
7. Round | 20/09/2008 | Stockport County | - | Swindon Town | 1:1 | ||||
8. Round | 27/09/2008 | Cheltenham Town | - | Stockport County | 2:2 |