| Workington v Darlington FC 08/11/1958 | View match | |
| Accrington Stanley (1891) v Workington 15/11/1958 | View match | |
| Workington v Millwall FC 22/11/1958 | View match | |
| Aldershot F.C v Workington 29/11/1958 | View match | |
| Workington v Gateshead 05/12/1958 | View match | |
| Oldham Athletic FC v Workington 13/12/1958 | View match | |
| Workington v Bradford Park Avenue 20/12/1958 | View match | |
| Carlisle United FC v Workington 26/12/1958 | View match | |
| Workington v Carlisle United FC 27/12/1958 | View match | |
| Barrow v Workington 01/01/1959 | View match | |
| Chester City FC v Workington 31/01/1959 | View match | |
| Workington v Watford FC 07/02/1959 | View match |