| Leyton Orient FC v Huddersfield Town FC 01/11/1958 | £10.00 | |
| Leyton Orient FC v Huddersfield Town FC 01/11/1958 | £10.00 | |
| Liverpool FC v Leyton Orient FC 08/11/1958 | View match | |
| Leyton Orient FC v Middlesbrough FC 15/11/1958 | £10.00 | |
| Charlton Athletic FC v Leyton Orient FC 22/11/1958 | View match | |
| Leyton Orient FC v Bristol City FC 29/11/1958 | £10.00 | |
| Cardiff City FC v Leyton Orient FC 06/12/1958 | View match | |
| Leyton Orient FC v Grimsby Town FC 13/12/1958 | £6.00 | |
| Bristol Rovers FC v Leyton Orient FC 20/12/1958 | View match | |
| Leyton Orient FC v Stoke City FC 26/12/1958 | View match | |
| Stoke City FC v Leyton Orient FC 27/12/1958 | View match | |
| Sunderland FC v Leyton Orient FC 01/01/1959 | View match |