| Leyton Orient FC v Derby County FC 03/01/1959 | View match | |
| Blackburn Rovers FC v Leyton Orient FC 10/01/1959 | View match | |
| Scunthorpe United FC v Leyton Orient FC 31/01/1959 | View match | |
| Leyton Orient FC v Sheffield Wednesday FC 07/02/1959 | View match | |
| Fulham FC v Leyton Orient FC 14/02/1959 | £4.00 | |
| Leyton Orient FC v Lincoln City FC 21/02/1959 | View match | |
| Leyton Orient FC v Liverpool FC 28/02/1959 | £10.00 | |
| Sheffield United FC v Leyton Orient FC 07/03/1959 | View match | |
| Leyton Orient FC v Brighton & Hove Albion FC 14/03/1959 | View match | |
| Huddersfield Town FC v Leyton Orient FC 21/03/1959 | View match | |
| Leyton Orient FC v Rotherham United FC 28/03/1959 | View match | |
| Leyton Orient FC v Sunderland FC 30/03/1959 | £10.00 |