| Bristol City FC v Middlesbrough FC 29/08/2009 | View match | |
| Middlesbrough FC v Ipswich Town FC 12/09/2009 | £5.50 | |
| Sheffield Wednesday FC v Middlesbrough FC 15/09/2009 | View match | |
| Middlesbrough FC v West Bromwich Albion FC 19/09/2009 | £4.80 | |
| Coventry City FC v Middlesbrough FC 26/09/2009 | View match | |
| Middlesbrough FC v Leicester City FC 29/09/2009 | £4.80 | |
| Reading FC v Middlesbrough FC 03/10/2009 | View match | |
| Middlesbrough FC v Watford FC 17/10/2009 | View match | |
| Middlesbrough FC v Derby County FC 20/10/2009 | £4.90 | |
| Preston North End FC v Middlesbrough FC 24/10/2009 | View match | |
| Middlesbrough FC v Plymouth Argyle FC 31/10/2009 | £4.80 | |
| Crystal Palace FC v Middlesbrough FC 07/11/2009 | View match |