| Workington v Torquay United FC 14/10/1966 | View match | |
| Oxford United FC v Workington 19/10/1966 | View match | |
| Brighton & Hove Albion FC v Workington 22/10/1966 | £1.00 | |
| Brighton & Hove Albion FC v Workington 22/10/1966 | £4.50 | |
| Workington v Darlington FC 28/10/1966 | View match | |
| Queens Park Rangers FC v Workington 05/11/1966 | View match | |
| Workington v Watford FC 12/11/1966 | View match | |
| Workington v Oxford United FC 16/11/1966 | View match | |
| Swindon Town FC v Workington 19/11/1966 | View match | |
| South Shields AFC v Workington 26/11/1966 | View match | |
| Doncaster Rovers FC v Workington 03/12/1966 | £8.99 | |
| Workington v Mansfield Town FC 10/12/1966 | View match |