| Nuneaton Borough v Middlesbrough FC 07/01/2006 | View match | |
| Arsenal FC v Middlesbrough FC 14/01/2006 | View match | |
| Middlesbrough FC v Nuneaton Borough 17/01/2006 | View match | |
| Middlesbrough FC v Wigan Athletic FC 21/01/2006 | View match | |
| Coventry City FC v Middlesbrough FC 28/01/2006 | £5.50 | |
| Sunderland FC v Middlesbrough FC 31/01/2006 | View match | |
| Middlesbrough FC v Aston Villa FC 04/02/2006 | View match | |
| Middlesbrough FC v Coventry City FC 08/02/2006 | £4.80 | |
| Middlesbrough FC v Chelsea FC 11/02/2006 | View match | |
| VfB Stuttgart v Middlesbrough FC 16/02/2006 | View match | |
| Preston North End FC v Middlesbrough FC 19/02/2006 | £4.80 | |
| Middlesbrough FC v VfB Stuttgart 23/02/2006 | £4.80 |