| Hartlepool United v Workington 14/02/1959 | View match | |
| Workington v Southport 21/02/1959 | View match | |
| Gillingham FC v Workington 28/02/1959 | View match | |
| Port Vale FC v Workington 02/03/1959 | View match | |
| Workington v Exeter City FC 07/03/1959 | View match | |
| Coventry City FC v Workington 14/03/1959 | View match | |
| Workington v Crystal Palace FC 16/03/1959 | View match | |
| Workington v Shrewsbury Town FC 21/03/1959 | View match | |
| York City FC v Workington 27/03/1959 | View match | |
| Darlington FC v Workington 28/03/1959 | View match | |
| Workington v York City FC 30/03/1959 | View match | |
| Workington v Walsall FC 04/04/1959 | View match |