| 21. Round | 02/01/2006 | Newcastle United | - | Middlesbrough FC | 2:2 | ||||
| 22. Round | 14/01/2006 | Arsenal FC | - | Middlesbrough FC | 7:0 |  |
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| 23. Round | 21/01/2006 | Middlesbrough FC | - | Wigan Athletic | 2:3 | ||||
| 24. Round | 31/01/2006 | Sunderland AFC | - | Middlesbrough FC | 0:3 | ||||
| 25. Round | 04/02/2006 | Middlesbrough FC | - | Aston Villa | 0:4 | ||||
| 27. Round | 26/02/2006 | West Bromwich Albion | - | Middlesbrough FC | 0:2 | |
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| 28. Round | 04/03/2006 | Middlesbrough FC | - | Birmingham City | 1:0 | ||||
| 29. Round | 12/03/2006 | Charlton Athletic | - | Middlesbrough FC | 2:1 | ||||
| 31. Round | 26/03/2006 | Middlesbrough FC | - | Bolton Wanderers | 4:3 | ||||
| 32. Round | 02/04/2006 | Manchester City | - | Middlesbrough FC | 0:1 |  |
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| 37. Round | 29/04/2006 | Middlesbrough FC | - | Everton FC | 0:1 | |
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| 36. Round | 01/05/2006 | Manchester United | - | Middlesbrough FC | 0:0 | ||||
| 19. Round | 03/05/2006 | Bolton Wanderers | - | Middlesbrough FC | 1:1 | |
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| 38. Round | 07/05/2006 | Fulham FC | - | Middlesbrough FC | 1:0 |
England
