| Birmingham City FC v Middlesbrough FC 23/08/1965 | £2.50 | |
| Preston North End FC v Middlesbrough FC 11/09/1965 | £4.50 | |
| Preston North End FC v Middlesbrough FC 11/09/1965 | £5.00 | |
| Middlesbrough FC v Charlton Athletic FC 18/09/1965 | £5.00 | |
| Tottenham Hotspur FC v Middlesbrough FC 22/01/1966 | £1.50 | |
| 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 | |
| Hull City FC v Middlesbrough FC 31/08/1968 | £2.00 |