| 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 | £4.80 | |
| Fulham FC v Middlesbrough FC 20/12/2008 | £5.00 | |
| Middlesbrough FC v Everton FC 26/12/2008 | £4.80 | |
| Manchester United FC v Middlesbrough FC 29/12/2008 | £5.00 | |
| Middlesbrough FC v Barrow 03/01/2009 | £4.80 | |
| Middlesbrough FC v Sunderland FC 10/01/2009 | £4.80 | |
| West Bromwich Albion FC v Middlesbrough FC 17/01/2009 | £5.50 | |
| Wolverhampton Wanderers FC v Middlesbrough FC 24/01/2009 | £4.90 |