1. Round | 07/08/2009 | Middlesbrough FC | - | Sheffield United | 0:0 | ||||
2. Round | 15/08/2009 | Swansea City | - | Middlesbrough FC | 0:3 | ||||
3. Round | 18/08/2009 | Scunthorpe United | - | Middlesbrough FC | 0:2 | ||||
4. Round | 22/08/2009 | Middlesbrough FC | - | Doncaster Rovers | 2:0 | ||||
5. Round | 29/08/2009 | Bristol City | - | Middlesbrough FC | 2:1 | ||||
6. Round | 12/09/2009 | Middlesbrough FC | - | Ipswich Town | 3:1 | ||||
7. Round | 15/09/2009 | Sheffield Wednesday | - | Middlesbrough FC | 1:3 | ||||
8. Round | 19/09/2009 | Middlesbrough FC | - | West Bromwich Albion | 0:5 | ||||
9. Round | 26/09/2009 | Coventry City | - | Middlesbrough FC | 2:2 | ||||
10. Round | 29/09/2009 | Middlesbrough FC | - | Leicester City | 0:1 | ||||
11. Round | 03/10/2009 | Reading FC | - | Middlesbrough FC | 0:2 | ||||
13. Round | 20/10/2009 | Middlesbrough FC | - | Derby County | 2:0 | ||||
14. Round | 24/10/2009 | Preston North End | - | Middlesbrough FC | 2:2 | ||||
15. Round | 31/10/2009 | Middlesbrough FC | - | Plymouth Argyle | 0:1 | ||||
21. Round | 13/12/2009 | Middlesbrough FC | - | Cardiff City | 0:1 | ||||
38. Round | 20/03/2010 | Middlesbrough FC | - | Reading FC | 1:1 |