| Charlton Athletic FC v Leyton Orient FC 19/03/1960 | View match | |
| Leyton Orient FC v Derby County FC 26/03/1960 | View match | |
| Leyton Orient FC v Derby County FC 26/03/1960 | View match | |
| Plymouth Argyle FC v Leyton Orient FC 02/04/1960 | View match | |
| Leyton Orient FC v Liverpool FC 09/04/1960 | £7.50 | |
| Romford v Leyton Orient FC 11/04/1960 | £12.50 | |
| Leyton Orient FC v Swansea Town 15/04/1960 | View match | |
| Scunthorpe United FC v Leyton Orient FC 16/04/1960 | View match | |
| Swansea Town v Leyton Orient FC 18/04/1960 | View match | |
| Leyton Orient FC v Bristol City FC 23/04/1960 | View match | |
| Middlesbrough FC v Leyton Orient FC 30/04/1960 | View match | |
| Leyton Orient FC v Ipswich Town FC 20/08/1960 | View match |