| Middlesbrough FC v Portsmouth FC 03/05/2008 | View match | |
| Middlesbrough FC v Manchester City FC 11/05/2008 | View match | |
| Middlesbrough FC v Tottenham Hotspur FC 16/08/2008 | £8.50 | |
| Middlesbrough FC v Tottenham Hotspur FC 16/08/2008 | £9.50 | |
| Liverpool FC v Middlesbrough FC 23/08/2008 | £4.80 | |
| 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 |