| West Ham United FC v Middlesbrough FC 14/02/2009 | £4.90 | |
| Middlesbrough FC v Wigan Athletic FC 21/02/2009 | £4.80 | |
| Middlesbrough FC v Liverpool FC 28/02/2009 | £4.80 | |
| Tottenham Hotspur FC v Middlesbrough FC 04/03/2009 | £5.00 | |
| Tottenham Hotspur FC v Middlesbrough FC 04/03/2009 | £4.80 | |
| Everton FC v Middlesbrough FC 08/03/2009 | £4.80 | |
| Middlesbrough FC v Portsmouth FC 14/03/2009 | £4.80 | |
| Stoke City FC v Middlesbrough FC 21/03/2009 | £4.80 | |
| Bolton Wanderers FC v Middlesbrough FC 04/04/2009 | £4.80 | |
| Middlesbrough FC v Hull City FC 11/04/2009 | £4.80 | |
| Middlesbrough FC v Fulham FC 18/04/2009 | £4.80 | |
| Arsenal FC v Middlesbrough FC 26/04/2009 | £4.80 |