| Middlesbrough FC v Derby County FC 22/03/2008 | £4.60 | |
| Chelsea FC v Middlesbrough FC 30/03/2008 | £4.80 | |
| Middlesbrough FC v Manchester United FC 06/04/2008 | £6.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 12/04/2008 | £4.60 | |
| Tottenham Hotspur FC v Middlesbrough FC 12/04/2008 | £4.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 12/04/2008 | £5.00 | |
| Middlesbrough FC v Bolton Wanderers FC 19/04/2008 | £4.70 | |
| Sunderland FC v Middlesbrough FC 26/04/2008 | £4.80 | |
| Middlesbrough FC v Tottenham Hotspur FC 16/08/2008 | £9.50 | |
| Middlesbrough FC v Tottenham Hotspur FC 16/08/2008 | £8.50 | |
| Liverpool FC v Middlesbrough FC 23/08/2008 | £4.80 | |
| Portsmouth FC v Middlesbrough FC 13/09/2008 | £4.80 |