| 11. Jornada | 19.10.2008 | Chester City | - | Port Vale FC | 1:2 | ||||
| 12. Jornada | 21.10.2008 | Rochdale AFC | - | Chester City | 6:1 | ||||
| 13. Jornada | 25.10.2008 | Gillingham FC | - | Chester City | 2:0 | ||||
| 14. Jornada | 28.10.2008 | Chester City | - | Brentford FC | 3:0 | ||||
| 15. Jornada | 01.11.2008 | Exeter City | - | Chester City | 2:0 | ||||
| 16. Jornada | 15.11.2008 | Chester City | - | Morecambe FC | 1:2 |  |
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| 17. Jornada | 22.11.2008 | Chester City | - | Aldershot Town | 0:1 | ||||
| 21. Jornada | 20.12.2008 | Bradford City | - | Chester City | 0:0 | ||||
| 22. Jornada | 26.12.2008 | Chester City | - | Accrington Stanley | 2:0 | ||||
| 23. Jornada | 28.12.2008 | Macclesfield Town | - | Chester City | 3:1 |
Inglaterra