| Chesterfield FC v Workington 23/11/1957 | View match | |
| Workington v Tranmere Rovers FC 30/11/1957 | View match | |
| Oldham Athletic FC v Workington 07/12/1957 | View match | |
| Workington v Bradford Park Avenue 14/12/1957 | View match | |
| Halifax Town A.F.C v Workington 21/12/1957 | View match | |
| Carlisle United FC v Workington 25/12/1957 | View match | |
| Workington v Carlisle United FC 26/12/1957 | View match | |
| Workington v Rochdale FC 28/12/1957 | View match | |
| Workington v Manchester United FC 04/01/1958 | View match | |
| Crewe Alexandra FC v Workington 11/01/1958 | View match | |
| Workington v Wrexham FC 18/01/1958 | View match | |
| Workington v Chester City FC 25/01/1958 | View match |