| 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 | |
| Everton FC v Middlesbrough FC 16/11/2008 | £5.50 | |
| Middlesbrough FC v Bolton Wanderers FC 22/11/2008 | £4.80 | |
| Middlesbrough FC v Newcastle United FC 29/11/2008 | £4.80 | |
| Hull City FC v Middlesbrough FC 06/12/2008 | £4.90 | |
| Middlesbrough FC v Arsenal FC 13/12/2008 | £4.80 | |
| Fulham FC v Middlesbrough FC 20/12/2008 | £5.00 | |
| Fulham FC v Middlesbrough FC 20/12/2008 | £4.80 |