| 4. Ronde | 30.08.2008 | Chester City | - | Barnet FC | 5:1 | ||||
| 5. Ronde | 06.09.2008 | Chester City | - | Bury FC | 1:1 | ||||
| 6. Ronde | 13.09.2008 | Grimsby Town | - | Chester City | 1:3 | ||||
| 7. Ronde | 21.09.2008 | Chester City | - | Shrewsbury Town | 1:1 | ||||
| 8. Ronde | 27.09.2008 | Luton Town | - | Chester City | 1:1 | ||||
| 9. Ronde | 04.10.2008 | Chester City | - | Lincoln City | 0:2 | ||||
| 11. Ronde | 19.10.2008 | Chester City | - | Port Vale FC | 1:2 |  |
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| 12. Ronde | 21.10.2008 | Rochdale AFC | - | Chester City | 6:1 | ||||
| 23. Ronde | 28.12.2008 | Macclesfield Town | - | Chester City | 3:1 |
Engeland