| Ipswich Town FC v Leyton Orient FC 11/04/1966 | View match | |
| Carlisle United FC v Leyton Orient FC 15/04/1966 | View match | |
| Leyton Orient FC v Middlesbrough FC 18/04/1966 | View match | |
| Leyton Orient FC v Coventry City FC 23/04/1966 | View match | |
| Bristol City FC v Leyton Orient FC 30/04/1966 | View match | |
| Leyton Orient FC v Manchester City FC 07/05/1966 | £12.50 | |
| Leyton Orient FC v Southampton FC 09/05/1966 | View match | |
| Oldham Athletic FC v Leyton Orient FC 20/08/1966 | £4.00 | |
| Brighton & Hove Albion FC v Leyton Orient FC 24/08/1966 | £4.50 | |
| Brighton & Hove Albion FC v Leyton Orient FC 24/08/1966 | £4.00 | |
| Leyton Orient FC v Scunthorpe United FC 27/08/1966 | £6.50 | |
| Workington v Leyton Orient FC 02/09/1966 | View match |