| Crystal Palace FC v Chester City FC 27/08/1958 | View match | |
| Crewe Alexandra FC v Chester City FC 30/08/1958 | £9.99 | |
| Chester City FC v Crystal Palace FC 03/09/1958 | View match | |
| Chester City FC v Northampton Town FC 06/09/1958 | View match | |
| Walsall FC v Chester City FC 11/09/1958 | View match | |
| Workington v Chester City FC 13/09/1958 | View match | |
| Chester City FC v Walsall FC 17/09/1958 | View match | |
| Chester City FC v York City FC 20/09/1958 | View match | |
| Bradford Park Avenue v Chester City FC 27/09/1958 | View match | |
| Chester City FC v Watford FC 01/10/1958 | View match | |
| Chester City FC v Port Vale FC 04/10/1958 | View match | |
| Chester City FC v Hartlepool United 08/10/1958 | View match |