| Workington v Chester City FC 13/09/1958 | View match | |
| Crewe Alexandra FC v Workington 18/09/1958 | View match | |
| Watford FC v Workington 20/09/1958 | View match | |
| Northampton Town FC v Workington 25/09/1958 | View match | |
| Workington v Hartlepool United 27/09/1958 | View match | |
| Workington v Northampton Town FC 01/10/1958 | View match | |
| Southport v Workington 04/10/1958 | View match | |
| Workington v Barrow 08/10/1958 | View match | |
| Workington v Gillingham FC 11/10/1958 | View match | |
| Exeter City FC v Workington 18/10/1958 | View match | |
| Workington v Coventry City FC 25/10/1958 | View match | |
| Shrewsbury Town FC v Workington 01/11/1958 | View match |