| Tottenham Hotspur FC v Middlesbrough FC 22/01/1966 | £1.50 | |
| Manchester City FC v Middlesbrough FC 29/01/1966 | £7.50 | |
| Reading FC v Middlesbrough FC 22/10/1966 | £5.00 | |
| Middlesbrough FC v Brighton & Hove Albion FC 10/12/1966 | £9.99 | |
| Leyton Orient FC v Middlesbrough FC 10/04/1967 | £5.00 | |
| Brighton & Hove Albion FC v Middlesbrough FC 06/05/1967 | £7.99 | |
| Hull City FC v Middlesbrough FC 23/09/1967 | £4.50 | |
| Queens Park Rangers FC v Middlesbrough FC 18/11/1967 | £3.00 | |
| Middlesbrough FC v Hull City FC 27/01/1968 | £5.00 | |
| Hull City FC v Middlesbrough FC 31/01/1968 | £4.50 | |
| Middlesbrough FC v Hull City FC 03/02/1968 | £4.50 | |
| Hull City FC v Middlesbrough FC 07/02/1968 | £13.50 |