| Aldershot Town F.C v Chester City FC 25/04/2009 | View match | |
| Chester City FC v Cambridge United FC 15/08/2009 | View match | |
| Oxford United FC v Chester City FC 18/08/2009 | View match | |
| Luton Town FC v Chester City FC 22/08/2009 | £7.50 | |
| Chester City FC v Mansfield Town FC 29/08/2009 | View match | |
| Altrincham v Chester City FC 31/08/2009 | View match | |
| Chester City FC v Histon 05/09/2009 | View match | |
| Chester City FC v Tamworth 08/09/2009 | View match | |
| Eastbourne Borough v Chester City FC 12/09/2009 | View match | |
| Chester City FC v Gateshead 15/09/2009 | View match | |
| Chester City FC v Stevenage Borough FC 19/09/2009 | View match | |
| Salisbury City v Chester City FC 22/09/2009 | View match |