4. Round | 30/08/2008 | Chester City | - | Barnet FC | 5:1 | ||||
5. Round | 06/09/2008 | Chester City | - | Bury FC | 1:1 | ||||
6. Round | 13/09/2008 | Grimsby Town | - | Chester City | 1:3 | ||||
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 | ||||
11. Round | 19/10/2008 | Chester City | - | Port Vale FC | 1:2 | ||||
12. Round | 21/10/2008 | Rochdale AFC | - | Chester City | 6:1 | ||||
23. Round | 28/12/2008 | Macclesfield Town | - | Chester City | 3:1 |