| Derby County FC v Leyton Orient FC 30/08/1958 | View match | |
| Leyton Orient FC v Ipswich Town FC 04/09/1958 | £8.99 | |
| Leyton Orient FC v Barnsley FC 06/09/1958 | View match | |
| Swansea Town v Leyton Orient FC 11/09/1958 | View match | |
| Leyton Orient FC v Scunthorpe United FC 13/09/1958 | View match | |
| Leyton Orient FC v Swansea Town 18/09/1958 | £10.00 | |
| Sheffield Wednesday FC v Leyton Orient FC 20/09/1958 | View match | |
| Leyton Orient FC v Fulham FC 27/09/1958 | £10.00 | |
| Lincoln City FC v Leyton Orient FC 04/10/1958 | View match | |
| Rotherham United FC v Leyton Orient FC 11/10/1958 | View match | |
| Leyton Orient FC v Sheffield United FC 18/10/1958 | View match | |
| Brighton & Hove Albion FC v Leyton Orient FC 25/10/1958 | £9.99 |