| 1. Round | 13/08/2005 | Middlesbrough FC | - | Liverpool FC | 0:0 | ||||
| 2. Round | 20/08/2005 | Tottenham Hotspur | - | Middlesbrough FC | 2:0 | ||||
| 4. Round | 28/08/2005 | Middlesbrough FC | - | Charlton Athletic | 0:3 | ||||
| 8. Round | 02/10/2005 | Aston Villa | - | Middlesbrough FC | 2:3 | ||||
| 9. Round | 15/10/2005 | Middlesbrough FC | - | Portsmouth FC | 1:1 | ||||
| 10. Round | 23/10/2005 | West Ham United | - | Middlesbrough FC | 2:1 | ||||
| 11. Round | 29/10/2005 | Middlesbrough FC | - | Manchester United | 4:1 |  |
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| 12. Round | 06/11/2005 | Everton FC | - | Middlesbrough FC | 1:0 | ||||
| 18. Round | 26/12/2005 | Middlesbrough FC | - | Blackburn Rovers | 0:2 |  |
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| 20. Round | 31/12/2005 | Middlesbrough FC | - | Manchester City | 0:0 | ||||
| 21. Round | 02/01/2006 | Newcastle United | - | Middlesbrough FC | 2:2 | ||||
| 22. Round | 14/01/2006 | Arsenal FC | - | Middlesbrough FC | 7:0 | ||||
| 24. Round | 31/01/2006 | Sunderland AFC | - | Middlesbrough FC | 0:3 | ||||
| 25. Round | 04/02/2006 | Middlesbrough FC | - | Aston Villa | 0:4 | |
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| 26. Round | 11/02/2006 | Middlesbrough FC | - | Chelsea FC | 3:0 | ||||
| 27. Round | 26/02/2006 | West Bromwich Albion | - | Middlesbrough FC | 0:2 | ||||
| 28. Round | 04/03/2006 | Middlesbrough FC | - | Birmingham City | 1:0 |
Spain