| Peterborough United FC v Workington 11/04/1966 | View match | |
| Scunthorpe United FC v Workington 16/04/1966 | View match | |
| Workington v Peterborough United FC 21/04/1966 | View match | |
| Workington v Watford FC 23/04/1966 | View match | |
| Workington v Bristol Rovers FC 26/04/1966 | View match | |
| Oldham Athletic FC v Workington 30/04/1966 | View match | |
| Swindon Town FC v Workington 03/05/1966 | View match | |
| Workington v Gillingham FC 07/05/1966 | View match | |
| Workington v Reading FC 09/05/1966 | View match | |
| Brighton & Hove Albion FC v Workington 20/05/1966 | £3.50 | |
| Brighton & Hove Albion FC v Workington 20/05/1966 | £1.00 | |
| Workington v Mansfield Town FC 27/05/1966 | View match |