| Leyton Orient FC v Aston Villa FC 13/02/1960 | £8.99 | |
| Sunderland FC v Leyton Orient FC 20/02/1960 | View match | |
| Leyton Orient FC v Cardiff City FC 27/02/1960 | View match | |
| Hull City FC v Leyton Orient FC 05/03/1960 | View match | |
| Arsenal FC v Leyton Orient FC 12/03/1960 | View match | |
| Leyton Orient FC v Sheffield United FC 17/03/1960 | £5.50 | |
| 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 |