| Barnet FC v Chester City FC 07/03/2009 | View match | |
| Bury FC v Chester City FC 21/03/2009 | View match | |
| Notts County FC v Chester City FC 04/04/2009 | View match | |
| Accrington Stanley FC v Chester City FC 13/04/2009 | View match | |
| 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 |