| Workington v Barrow 03/09/1960 | View match | |
| Workington v Oldham Athletic FC 07/09/1960 | View match | |
| Millwall FC v Workington 10/09/1960 | View match | |
| Oldham Athletic FC v Workington 12/09/1960 | View match | |
| Workington v Accrington Stanley (1891) 17/09/1960 | £15.00 | |
| Workington v Aldershot F.C 21/09/1960 | View match | |
| York City FC v Workington 24/09/1960 | View match | |
| Aldershot F.C v Workington 28/09/1960 | View match | |
| Workington v Crewe Alexandra FC 01/10/1960 | View match | |
| Workington v Chester City FC 05/10/1960 | View match | |
| Mansfield Town FC v Workington 08/10/1960 | View match | |
| Workington v Stockport County FC 15/10/1960 | View match |