7. Round | 21/09/2008 | Chester City | - | Shrewsbury Town | 1:1 | ||||
8. Round | 27/09/2008 | Luton Town | - | Chester City | 1:1 | ||||
9. Round | 04/10/2008 | Chester City | - | Lincoln City | 0:2 | ||||
10. Round | 11/10/2008 | Chesterfield FC | - | Chester City | 1:1 | ||||
11. Round | 19/10/2008 | Chester City | - | Port Vale FC | 1:2 | ||||
17. Round | 22/11/2008 | Chester City | - | Aldershot Town | 0:1 | ||||
18. Round | 25/11/2008 | Darlington FC | - | Chester City | 1:2 | ||||
19. Round | 06/12/2008 | AFC Bournemouth | - | Chester City | 1:0 |