| 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 | £4.00 | |
| Leyton Orient FC v Scunthorpe United FC 27/08/1966 | View match | |
| Workington v Leyton Orient FC 02/09/1966 | View match | |
| Leyton Orient FC v Torquay United FC 05/09/1966 | View match | |
| Leyton Orient FC v Gillingham FC 09/09/1966 | View match | |
| Leyton Orient FC v Peterborough United FC 17/09/1966 | View match |