| Bournemouth & Boscombe v Leyton Orient FC 24/09/1966 | View match | |
| Torquay United FC v Leyton Orient FC 28/09/1966 | View match | |
| Leyton Orient FC v Swansea Town 01/10/1966 | View match | |
| Brighton & Hove Albion FC v Leyton Orient FC 08/10/1966 | £2.50 | |
| Leyton Orient FC v Darlington FC 15/10/1966 | View match | |
| Colchester United FC v Leyton Orient FC 17/10/1966 | View match | |
| Queens Park Rangers FC v Leyton Orient FC 22/10/1966 | View match | |
| Leyton Orient FC v Watford FC 29/10/1966 | £5.50 | |
| Millwall FC v Leyton Orient FC 31/10/1966 | View match | |
| Swindon Town FC v Leyton Orient FC 05/11/1966 | View match | |
| Leyton Orient FC v Reading FC 11/11/1966 | £4.50 | |
| Leyton Orient FC v Colchester United FC 14/11/1966 | £5.00 |