| 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 | |
| Arsenal FC v Middlesbrough FC 26/04/2009 | £5.00 | |
| Middlesbrough FC v Manchester United FC 02/05/2009 | £5.50 | |
| Middlesbrough FC v Aston Villa FC 16/05/2009 | £4.80 | |
| West Ham United FC v Middlesbrough FC 24/05/2009 | £4.50 | |
| West Ham United FC v Middlesbrough FC 24/05/2009 | £4.90 |