12. Round | 21/10/2008 | Milton Keynes Dons | - | Stockport County | 1:2 | ||||
13. Round | 25/10/2008 | Hereford United | - | Stockport County | 0:1 | ||||
14. Round | 28/10/2008 | Stockport County | - | Tranmere Rovers | 0:0 | ||||
15. Round | 01/11/2008 | Stockport County | - | Carlisle United | 3:0 | ||||
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 |