| Leyton Orient FC v Plymouth Argyle FC 18/09/1965 | View match | |
| Leyton Orient FC v Coventry City FC 22/09/1965 | View match | |
| Portsmouth FC v Leyton Orient FC 25/09/1965 | View match | |
| Leyton Orient FC v Bolton Wanderers FC 02/10/1965 | View match | |
| Leyton Orient FC v Wolverhampton Wanderers FC 09/10/1965 | View match | |
| Norwich City FC v Leyton Orient FC 16/10/1965 | View match | |
| Leyton Orient FC v Bury FC 23/10/1965 | View match | |
| Southampton FC v Leyton Orient FC 30/10/1965 | £7.50 | |
| Southampton FC v Leyton Orient FC 30/10/1965 | £7.50 | |
| Leyton Orient FC v Derby County FC 06/11/1965 | View match | |
| Cardiff City FC v Leyton Orient FC 13/11/1965 | View match | |
| Leyton Orient FC v Carlisle United FC 20/11/1965 | View match |