| Middlesbrough FC v Birmingham City FC 09/08/2014 | £5.50 | |
| Oldham Athletic FC v Middlesbrough FC 12/08/2014 | View match | |
| Leeds United FC v Middlesbrough FC 16/08/2014 | View match | |
| Bolton Wanderers FC v Middlesbrough FC 19/08/2014 | £5.50 | |
| Middlesbrough FC v Sheffield Wednesday FC 23/08/2014 | View match | |
| Middlesbrough FC v Preston North End FC 26/08/2014 | View match | |
| Middlesbrough FC v Reading FC 30/08/2014 | View match | |
| Huddersfield Town FC v Middlesbrough FC 13/09/2014 | View match | |
| Cardiff City FC v Middlesbrough FC 16/09/2014 | View match | |
| Middlesbrough FC v Brentford FC 20/09/2014 | View match | |
| Liverpool FC v Middlesbrough FC 23/09/2014 | View match | |
| Liverpool FC v Middlesbrough FC 23/09/2014 | View match |