| West Bromwich Albion FC v Middlesbrough FC 17/01/2009 | £5.50 | |
| Wolverhampton Wanderers FC v Middlesbrough FC 24/01/2009 | £4.90 | |
| Chelsea FC v Middlesbrough FC 28/01/2009 | £3.99 | |
| Chelsea FC v Middlesbrough FC 28/01/2009 | £4.80 | |
| Manchester City FC v Middlesbrough FC 07/02/2009 | £4.90 | |
| West Ham United FC v Middlesbrough FC 14/02/2009 | £4.90 | |
| West Ham United FC v Middlesbrough FC 14/02/2009 | £5.00 | |
| Middlesbrough FC v Wigan Athletic FC 21/02/2009 | £4.80 | |
| Middlesbrough FC v West Ham United FC 25/02/2009 | £6.00 | |
| Middlesbrough FC v Liverpool FC 28/02/2009 | £4.80 | |
| Tottenham Hotspur FC v Middlesbrough FC 04/03/2009 | £5.00 | |
| Tottenham Hotspur FC v Middlesbrough FC 04/03/2009 | £4.80 |