| 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 | |
| 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 Brighton & Hove Albion FC 31/08/1960 | £12.99 | |
| Leyton Orient FC v Sheffield Wednesday FC 18/02/1961 | £9.99 | |
| Leyton Orient FC v Plymouth Argyle FC 07/03/1961 | £7.00 | |
| Leyton Orient FC v Middlesbrough FC 14/03/1961 | £6.99 | |
| Leyton Orient FC v Huddersfield Town FC 21/03/1961 | £6.50 |