| 26. Ronde | 17.01.2009 | Chester City | - | Chesterfield FC | 1:3 | ||||
| 27. Ronde | 24.01.2009 | Lincoln City | - | Chester City | 1:1 | ||||
| 31. Ronde | 07.02.2009 | Brentford FC | - | Chester City | 3:0 | ||||
| 32. Ronde | 14.02.2009 | Morecambe FC | - | Chester City | 3:1 | ||||
| 25. Ronde | 17.02.2009 | Shrewsbury Town | - | Chester City | 1:0 | ||||
| 33. Ronde | 21.02.2009 | Chester City | - | Exeter City | 0:0 | ||||
| 34. Ronde | 28.02.2009 | Chester City | - | Dagenham & Redbridge | 2:2 | ||||
| 39. Ronde | 21.03.2009 | Bury FC | - | Chester City | 1:1 | ||||
| 40. Ronde | 28.03.2009 | Chester City | - | Bradford City | 0:0 | ||||
| 41. Ronde | 04.04.2009 | Notts County | - | Chester City | 1:2 | ||||
| 42. Ronde | 11.04.2009 | Chester City | - | Macclesfield Town | 0:2 | ||||
| 43. Ronde | 13.04.2009 | Accrington Stanley | - | Chester City | 0:1 | ||||
| 44. Ronde | 18.04.2009 | Chester City | - | AFC Bournemouth | 0:2 | ||||
| 45. Ronde | 25.04.2009 | Aldershot Town | - | Chester City | 2:2 | ||||
| 46. Ronde | 02.05.2009 | Chester City | - | Darlington FC | 1:2 |
Engeland