| Aldershot F.C v Workington 16/09/1959 | View match | |
| Workington v Oldham Athletic FC 19/09/1959 | View match | |
| Workington v Gillingham FC 24/09/1959 | View match | |
| Rochdale FC v Workington 26/09/1959 | View match | |
| Gillingham FC v Workington 30/09/1959 | View match | |
| Workington v Gateshead 03/10/1959 | View match | |
| Darlington FC v Workington 07/10/1959 | View match | |
| Notts County FC v Workington 10/10/1959 | View match | |
| Workington v Darlington FC 15/10/1959 | View match | |
| Workington v Walsall FC 17/10/1959 | View match | |
| Hartlepool United v Workington 24/10/1959 | View match | |
| Workington v Crewe Alexandra FC 31/10/1959 | View match |