15. Round | 01/11/2008 | Stockport County | - | Carlisle United | 3:0 | ||||
16. Round | 15/11/2008 | Millwall FC | - | Stockport County | 1:0 | ||||
17. Round | 22/11/2008 | Crewe Alexandra | - | Stockport County | 0:3 | ||||
18. Round | 25/11/2008 | Stockport County | - | Brighton & Hove Albion | 2:0 | ||||
19. Round | 06/12/2008 | Stockport County | - | Peterborough United | 1:3 | ||||
20. Round | 13/12/2008 | Yeovil Town | - | Stockport County | 2:4 | ||||
21. Round | 20/12/2008 | Stockport County | - | Bristol Rovers | 3:1 | ||||
22. Round | 26/12/2008 | Walsall FC | - | Stockport County | 1:0 | ||||
23. Round | 28/12/2008 | Stockport County | - | Leeds United | 1:3 |