| Stoke City FC v Leyton Orient FC 28/12/1957 | View match | |
| Leyton Orient FC v Reading FC 04/01/1958 | View match | |
| Leyton Orient FC v Bristol City FC 11/01/1958 | £10.00 | |
| Cardiff City FC v Leyton Orient FC 18/01/1958 | View match | |
| Cardiff City FC v Leyton Orient FC 25/01/1958 | View match | |
| Leyton Orient FC v Liverpool FC 01/02/1958 | View match | |
| Middlesbrough FC v Leyton Orient FC 08/02/1958 | View match | |
| Leyton Orient FC v West Ham United FC 20/02/1958 | View match | |
| Notts County FC v Leyton Orient FC 22/02/1958 | View match | |
| Leyton Orient FC v East Fife FC 01/03/1958 | View match | |
| Swansea Town v Leyton Orient FC 08/03/1958 | View match | |
| Leyton Orient FC v Fulham FC 13/03/1958 | View match |