| Leyton Orient FC v Hull City FC 17/10/1959 | View match | |
| Sheffield United FC v Leyton Orient FC 24/10/1959 | View match | |
| Leyton Orient FC v Middlesbrough FC 31/10/1959 | View match | |
| Derby County FC v Leyton Orient FC 07/11/1959 | View match | |
| Leyton Orient FC v Plymouth Argyle FC 14/11/1959 | View match | |
| Liverpool FC v Leyton Orient FC 21/11/1959 | View match | |
| Leyton Orient FC v Charlton Athletic FC 28/11/1959 | £5.50 | |
| Bristol City FC v Leyton Orient FC 05/12/1959 | View match | |
| Leyton Orient FC v Scunthorpe United FC 12/12/1959 | £5.00 | |
| Leyton Orient FC v Bristol Rovers FC 19/12/1959 | View match | |
| Leyton Orient FC v Portsmouth FC 26/12/1959 | £7.99 | |
| Portsmouth FC v Leyton Orient FC 28/12/1959 | View match |