| Workington v Stockport County FC 07/04/1958 | View match | |
| Tranmere Rovers FC v Workington 12/04/1958 | View match | |
| Workington v Accrington Stanley (1891) 19/04/1958 | £25.00 | |
| Workington v Mansfield Town FC 23/04/1958 | View match | |
| Bradford Park Avenue v Workington 26/04/1958 | View match | |
| York City FC v Workington 28/04/1958 | View match | |
| Bradford Park Avenue v Workington 23/08/1958 | View match | |
| Workington v Torquay United FC 25/08/1958 | View match | |
| Workington v Port Vale FC 30/08/1958 | £10.00 | |
| Torquay United FC v Workington 04/09/1958 | View match | |
| Crystal Palace FC v Workington 06/09/1958 | View match | |
| Workington v Crewe Alexandra FC 10/09/1958 | View match |