| Chester City FC v Workington 07/11/1959 | View match | |
| Southport v Workington 14/11/1959 | View match | |
| Workington v Southport 18/11/1959 | View match | |
| Bradford Park Avenue v Workington 21/11/1959 | View match | |
| Carlisle United FC v Workington 26/11/1959 | View match | |
| Workington v Stockport County FC 28/11/1959 | View match | |
| Workington v Halifax Town A.F.C 05/12/1959 | View match | |
| Watford FC v Workington 12/12/1959 | View match | |
| Workington v Millwall FC 19/12/1959 | View match | |
| Carlisle United FC v Workington 26/12/1959 | View match | |
| Workington v Carlisle United FC 29/12/1959 | View match | |
| Torquay United FC v Workington 02/01/1960 | View match |