11. Round | 19/10/2008 | Chester City | - | Port Vale FC | 1:2 | ||||
12. Round | 21/10/2008 | Rochdale AFC | - | Chester City | 6:1 | ||||
13. Round | 25/10/2008 | Gillingham FC | - | Chester City | 2:0 | ||||
14. Round | 28/10/2008 | Chester City | - | Brentford FC | 3:0 | ||||
15. Round | 01/11/2008 | Exeter City | - | Chester City | 2:0 | ||||
16. Round | 15/11/2008 | Chester City | - | Morecambe FC | 1:2 | ||||
17. Round | 22/11/2008 | Chester City | - | Aldershot Town | 0:1 | ||||
21. Round | 20/12/2008 | Bradford City | - | Chester City | 0:0 | ||||
22. Round | 26/12/2008 | Chester City | - | Accrington Stanley | 2:0 | ||||
23. Round | 28/12/2008 | Macclesfield Town | - | Chester City | 3:1 |