| Grimsby Town FC v Chester City FC 13/09/2008 | View match | |
| Luton Town FC v Chester City FC 27/09/2008 | £5.00 | |
| Chesterfield FC v Chester City FC 11/10/2008 | View match | |
| Rochdale FC v Chester City FC 21/10/2008 | View match | |
| Gillingham FC v Chester City FC 25/10/2008 | View match | |
| Exeter City FC v Chester City FC 01/11/2008 | View match | |
| Chester City FC v Millwall FC 08/11/2008 | View match | |
| Darlington FC v Chester City FC 25/11/2008 | View match | |
| AFC Bournemouth v Chester City FC 06/12/2008 | View match | |
| Bradford City FC v Chester City FC 20/12/2008 | View match | |
| Macclesfield Town FC v Chester City FC 28/12/2008 | View match | |
| Lincoln City FC v Chester City FC 24/01/2009 | View match |