| Walsall FC v Workington 09/04/1959 | View match | |
| Millwall FC v Workington 11/04/1959 | View match | |
| Workington v Aldershot F.C 18/04/1959 | View match | |
| Workington v Oldham Athletic FC 22/04/1959 | View match | |
| Gateshead v Workington 25/04/1959 | View match | |
| Millwall FC v Workington 22/08/1959 | View match | |
| Workington v Southport 27/08/1959 | View match | |
| Workington v Torquay United FC 29/08/1959 | View match | |
| Southport v Workington 01/09/1959 | View match | |
| Northampton Town FC v Workington 05/09/1959 | View match | |
| Workington v Aldershot F.C 10/09/1959 | View match | |
| Workington v Doncaster Rovers FC 12/09/1959 | View match |