| Leyton Orient FC v Sunderland FC 30/03/1959 | £10.00 | |
| Middlesbrough FC v Leyton Orient FC 04/04/1959 | View match | |
| Leyton Orient FC v Charlton Athletic FC 11/04/1959 | View match | |
| Bristol City FC v Leyton Orient FC 18/04/1959 | View match | |
| Grimsby Town FC v Leyton Orient FC 21/04/1959 | View match | |
| Leyton Orient FC v Cardiff City FC 25/04/1959 | View match | |
| Barnsley FC v Leyton Orient FC 29/04/1959 | View match | |
| Bristol Rovers FC v Leyton Orient FC 22/08/1959 | View match | |
| Leyton Orient FC v Stoke City FC 27/08/1959 | £6.00 | |
| Leyton Orient FC v Ipswich Town FC 29/08/1959 | View match | |
| Stoke City FC v Leyton Orient FC 02/09/1959 | View match | |
| Huddersfield Town FC v Leyton Orient FC 05/09/1959 | View match |