| 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 | |
| Middlesbrough FC v Manchester United FC 02/05/2009 | £5.50 | |
| Newcastle United FC v Middlesbrough FC 11/05/2009 | £4.80 | |
| Middlesbrough FC v Aston Villa FC 16/05/2009 | £4.80 | |
| West Ham United FC v Middlesbrough FC 24/05/2009 | £4.90 | |
| Middlesbrough FC v Ipswich Town FC 12/09/2009 | £5.50 | |
| Middlesbrough FC v West Bromwich Albion FC 19/09/2009 | £4.80 | |
| Middlesbrough FC v Leicester City FC 29/09/2009 | £4.80 | |
| Middlesbrough FC v Derby County FC 20/10/2009 | £4.90 |