| Middlesbrough FC v Yeovil Town FC 26/08/2008 | View match | |
| Middlesbrough FC v Stoke City FC 30/08/2008 | View match | |
| Portsmouth FC v Middlesbrough FC 13/09/2008 | £4.80 | |
| Sunderland FC v Middlesbrough FC 20/09/2008 | £4.90 | |
| Manchester United FC v Middlesbrough FC 23/09/2008 | £5.50 | |
| Middlesbrough FC v West Bromwich Albion FC 27/09/2008 | £5.30 | |
| Wigan Athletic FC v Middlesbrough FC 04/10/2008 | View match | |
| Middlesbrough FC v Chelsea FC 18/10/2008 | £6.50 | |
| Blackburn Rovers FC v Middlesbrough FC 25/10/2008 | £4.80 | |
| Middlesbrough FC v Manchester City FC 29/10/2008 | £4.80 | |
| Middlesbrough FC v West Ham United FC 01/11/2008 | £4.70 | |
| Aston Villa FC v Middlesbrough FC 09/11/2008 | £4.80 |