| Leyton Orient FC v Grimsby Town FC 13/12/1958 | £6.00 | |
| Fulham FC v Leyton Orient FC 14/02/1959 | £4.00 | |
| Leyton Orient FC v Liverpool FC 28/02/1959 | £10.00 | |
| Leyton Orient FC v Sunderland FC 30/03/1959 | £10.00 | |
| Leyton Orient FC v Stoke City FC 27/08/1959 | £6.00 | |
| Leyton Orient FC v Brighton & Hove Albion FC 10/09/1959 | £5.00 | |
| Leyton Orient FC v Charlton Athletic FC 28/11/1959 | £5.50 | |
| Leyton Orient FC v Scunthorpe United FC 12/12/1959 | £5.00 | |
| Leyton Orient FC v Portsmouth FC 26/12/1959 | £7.99 | |
| Leyton Orient FC v Huddersfield Town FC 16/01/1960 | £7.99 | |
| Leyton Orient FC v Aston Villa FC 13/02/1960 | £8.99 | |
| Leyton Orient FC v Sheffield United FC 17/03/1960 | £5.50 |