| Middlesbrough FC v Manchester City FC 05/12/1964 | £9.50 | |
| Bury FC v Middlesbrough FC 23/02/1965 | £8.50 | |
| Manchester City FC v Middlesbrough FC 06/03/1965 | £5.00 | |
| Birmingham City FC v Middlesbrough FC 23/08/1965 | £2.50 | |
| Preston North End FC v Middlesbrough FC 11/09/1965 | £5.00 | |
| Bury FC v Middlesbrough FC 30/10/1965 | £10.00 | |
| Tottenham Hotspur FC v Middlesbrough FC 22/01/1966 | £1.50 | |
| Manchester City FC v Middlesbrough FC 29/01/1966 | £7.50 | |
| Middlesbrough FC v Bury FC 09/04/1966 | £6.50 | |
| Queens Park Rangers FC v Middlesbrough FC 06/09/1966 | £5.00 | |
| Reading FC v Middlesbrough FC 22/10/1966 | £5.00 | |
| Middlesbrough FC v Brighton & Hove Albion FC 10/12/1966 | £9.99 |