| Coventry City FC v Leyton Orient FC 22/08/1953 | View match | |
| Brighton & Hove Albion FC v Leyton Orient FC 26/08/1953 | £26.99 | |
| Leyton Orient FC v Bournemouth & Boscombe 29/08/1953 | View match | |
| Leyton Orient FC v Brighton & Hove Albion FC 03/09/1953 | £45.99 | |
| Ipswich Town FC v Leyton Orient FC 05/09/1953 | View match | |
| Leyton Orient FC v Torquay United FC 10/09/1953 | View match | |
| Leyton Orient FC v Millwall FC 12/09/1953 | View match | |
| Torquay United FC v Leyton Orient FC 16/09/1953 | View match | |
| Leyton Orient FC v Bristol City FC 19/09/1953 | View match | |
| Leyton Orient FC v Gillingham FC 24/09/1953 | View match | |
| Reading FC v Leyton Orient FC 26/09/1953 | View match | |
| Gillingham FC v Leyton Orient FC 30/09/1953 | View match |