| Gillingham FC v Workington 27/08/1966 | View match | |
| Workington v Leyton Orient FC 02/09/1966 | View match | |
| Walsall FC v Workington 06/09/1966 | View match | |
| Bournemouth & Boscombe v Workington 10/09/1966 | View match | |
| Bury FC v Workington 14/09/1966 | £7.50 | |
| Workington v Swansea Town 16/09/1966 | View match | |
| Middlesbrough FC v Workington 24/09/1966 | View match | |
| Workington v Walsall FC 28/09/1966 | View match | |
| Grimsby Town FC v Workington 05/10/1966 | View match | |
| Peterborough United FC v Workington 08/10/1966 | View match | |
| Workington v Torquay United FC 14/10/1966 | View match | |
| Oxford United FC v Workington 19/10/1966 | View match |