| 7. Ronde | 21.09.2008 | Chester City | - | Shrewsbury Town | 1:1 |  |
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| 8. Ronde | 27.09.2008 | Luton Town | - | Chester City | 1:1 | |
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| 9. Ronde | 04.10.2008 | Chester City | - | Lincoln City | 0:2 | ||||
| 10. Ronde | 11.10.2008 | Chesterfield FC | - | Chester City | 1:1 | ||||
| 11. Ronde | 19.10.2008 | Chester City | - | Port Vale FC | 1:2 | ||||
| 17. Ronde | 22.11.2008 | Chester City | - | Aldershot Town | 0:1 | ||||
| 18. Ronde | 25.11.2008 | Darlington FC | - | Chester City | 1:2 | ||||
| 19. Ronde | 06.12.2008 | AFC Bournemouth | - | Chester City | 1:0 |
Engeland