1. Round | 09/08/2008 | Dagenham & Redbridge | - | Chester City | 6:0 | ||||
2. Round | 16/08/2008 | Chester City | - | Wycombe Wanderers | 0:2 | ||||
3. Round | 23/08/2008 | Rotherham United | - | Chester City | 3:1 | ||||
4. Round | 30/08/2008 | Chester City | - | Barnet FC | 5:1 | ||||
5. Round | 06/09/2008 | Chester City | - | Bury FC | 1:1 | ||||
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 |