| 4. Round | 20/08/2005 | Rushden & Diamonds FC | - | Chester City | 1:1 | ||||
| 6. Round | 29/08/2005 | Torquay United | - | Chester City | 0:1 | ||||
| 9. Round | 17/09/2005 | Chester City | - | Bristol Rovers | 4:0 | ||||
| 10. Round | 24/09/2005 | Stockport County | - | Chester City | 0:0 | ||||
| 15. Round | 22/10/2005 | Chester City | - | Bury FC | 1:1 |  |
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| 16. Round | 29/10/2005 | Shrewsbury Town | - | Chester City | 3:1 | ||||
| 18. Round | 19/11/2005 | Rochdale AFC | - | Chester City | 2:2 | ||||
| 22. Round | 17/12/2005 | Chester City | - | Rushden & Diamonds FC | 1:2 | ||||
| 23. Round | 26/12/2005 | Cheltenham Town | - | Chester City | 1:0 | ||||
| 29. Round | 21/01/2006 | Bristol Rovers | - | Chester City | 2:1 | ||||
| 27. Round | 24/01/2006 | Mansfield Town | - | Chester City | 1:2 | ||||
| 30. Round | 28/01/2006 | Chester City | - | Notts County | 0:2 | ||||
| 31. Round | 04/02/2006 | Carlisle United | - | Chester City | 5:0 | ||||
| 36. Round | 07/03/2006 | Chester City | - | Torquay United | 1:1 | ||||
| 38. Round | 18/03/2006 | Chester City | - | Cheltenham Town | 0:1 | ||||
| 44. Round | 22/04/2006 | Chester City | - | Barnet FC | 0:0 | ||||
| 45. Round | 29/04/2006 | Northampton Town | - | Chester City | 1:0 | ||||
| 46. Round | 06/05/2006 | Chester City | - | Shrewsbury Town | 0:1 |
England