| Liverpool FC v Leyton Orient FC 25/12/1956 | View match | |
| Leyton Orient FC v Liverpool FC 26/12/1956 | View match | |
| Bury FC v Leyton Orient FC 29/12/1956 | View match | |
| Leyton Orient FC v Chelsea FC 05/01/1957 | View match | |
| Leyton Orient FC v Grimsby Town FC 12/01/1957 | £10.00 | |
| Doncaster Rovers FC v Leyton Orient FC 19/01/1957 | View match | |
| Leyton Orient FC v Stoke City FC 02/02/1957 | View match | |
| Middlesbrough FC v Leyton Orient FC 09/02/1957 | View match | |
| West Ham United FC v Leyton Orient FC 16/02/1957 | View match | |
| Leyton Orient FC v Blackburn Rovers FC 23/02/1957 | View match | |
| Swansea Town v Leyton Orient FC 02/03/1957 | View match | |
| Leyton Orient FC v Sheffield United FC 09/03/1957 | £10.00 |