| Arsenal FC v Middlesbrough FC 20/08/1995 | £3.50 | |
| Arsenal FC v Middlesbrough FC 20/08/1995 | £2.00 | |
| Manchester City FC v Middlesbrough FC 23/09/1995 | £5.00 | |
| Rotherham United FC v Middlesbrough FC 03/10/1995 | £4.50 | |
| Sheffield Wednesday FC v Middlesbrough FC 15/10/1995 | £2.00 | |
| Blackburn Rovers FC v Middlesbrough FC 16/12/1995 | £4.00 | |
| Middlesbrough FC v West Ham United FC 23/12/1995 | £5.50 | |
| Southampton FC v Middlesbrough FC 20/01/1996 | £2.00 | |
| Chelsea FC v Middlesbrough FC 04/02/1996 | £4.50 | |
| Chelsea FC v Middlesbrough FC 04/02/1996 | £4.00 | |
| Coventry City FC v Middlesbrough FC 24/02/1996 | £3.50 | |
| West Ham United FC v Middlesbrough FC 09/03/1996 | £4.50 |