| Bury FC v Leyton Orient FC 15/01/1966 | £7.00 | |
| Leyton Orient FC v Norwich City FC 22/01/1966 | View match | |
| Huddersfield Town FC v Leyton Orient FC 29/01/1966 | View match | |
| Leyton Orient FC v Crystal Palace FC 05/02/1966 | View match | |
| Preston North End FC v Leyton Orient FC 19/02/1966 | £3.00 | |
| Preston North End FC v Leyton Orient FC 19/02/1966 | £4.50 | |
| Leyton Orient FC v Charlton Athletic FC 26/02/1966 | View match | |
| Plymouth Argyle FC v Leyton Orient FC 12/03/1966 | View match | |
| Leyton Orient FC v Portsmouth FC 19/03/1966 | View match | |
| Bolton Wanderers FC v Leyton Orient FC 26/03/1966 | View match | |
| Leyton Orient FC v Norwich City FC 28/03/1966 | View match | |
| Derby County FC v Leyton Orient FC 02/04/1966 | View match |