| Workington v Millwall FC 28/01/1966 | View match | |
| Bournemouth & Boscombe v Workington 05/02/1966 | View match | |
| Workington v Oxford United FC 11/02/1966 | View match | |
| Workington v Southend United FC 19/02/1966 | View match | |
| Oxford United FC v Workington 05/03/1966 | View match | |
| Workington v Shrewsbury Town FC 11/03/1966 | View match | |
| Workington v York City FC 15/03/1966 | View match | |
| Grimsby Town FC v Workington 19/03/1966 | View match | |
| Workington v Brentford FC 26/03/1966 | View match | |
| Workington v Walsall FC 30/03/1966 | View match | |
| Queens Park Rangers FC v Workington 02/04/1966 | View match | |
| Workington v Oldham Athletic FC 09/04/1966 | View match |