| Leyton Orient FC v Swansea Town 26/10/1957 | £10.00 | |
| Derby County FC v Leyton Orient FC 02/11/1957 | View match | |
| Leyton Orient FC v Bristol Rovers FC 09/11/1957 | £10.00 | |
| Lincoln City FC v Leyton Orient FC 16/11/1957 | View match | |
| Leyton Orient FC v Notts County FC 23/11/1957 | View match | |
| Ipswich Town FC v Leyton Orient FC 30/11/1957 | View match | |
| Leyton Orient FC v Blackburn Rovers FC 07/12/1957 | £10.00 | |
| Sheffield United FC v Leyton Orient FC 14/12/1957 | View match | |
| Leyton Orient FC v Grimsby Town FC 21/12/1957 | £10.00 | |
| Leyton Orient FC v Grimsby Town FC 21/12/1957 | £10.00 | |
| Leyton Orient FC v Rotherham United FC 25/12/1957 | View match | |
| Rotherham United FC v Leyton Orient FC 26/12/1957 | View match |