| h2h | 2009-02-28 | Middlesbrough |  | 2-0 |  | Liverpool | D27 | |||
| h2h | 2009-01-24 | Wolverhampton |  | 1-2 | | Middlesbrough | 4R | |||
| h2h | 2008-11-09 | Aston Villa |  | 1-2 | | Middlesbrough | D12 | |||
| h2h | 2008-01-29 | Middlesbrough | | 1-0 |  | Wigan Athletic | D24 | |||
| h2h | 2007-12-15 | Derby County |  | 0-1 | | Middlesbrough | D17 | |||
| h2h | 2007-09-01 | Middlesbrough | | 2-0 |  | Birmingham City | D5 | |||
| h2h | 2006-12-23 | Middlesbrough | | 2-0 |  | Charlton Athletic | D19 | |||
| h2h | 2006-09-09 | Arsenal |  | 1-1 | | Middlesbrough | D4 | |||
| h2h | 2006-01-14 | Arsenal | | 7-0 | | Middlesbrough | D22 | |||
| h2h | 2005-05-15 | Manchester City |  | 1-1 | | Middlesbrough | D38 |
| h2h | 2009-02-28 | Middlesbrough | | 2-0 | | Liverpool | D27 | |||
| h2h | 2008-11-15 | Bolton |  | 0-2 | | Liverpool | D13 | |||
| h2h | 2008-02-02 | Liverpool | | 3-0 |  | Sunderland | D25 | |||
| h2h | 2007-08-19 | Liverpool | | 1-1 |  | Chelsea | D3 | |||
| h2h | 2007-01-20 | Liverpool | | 2-0 | | Chelsea | D24 | |||
| h2h | 2006-12-26 | Blackburn Rovers |  | 1-0 | | Liverpool | D20 | |||
| h2h | 2006-11-25 | Liverpool | | 1-0 | | Manchester City | D14 | |||
| h2h | 2006-08-19 | Sheffield United |  | 1-1 | | Liverpool | D1 | |||
| h2h | 2006-04-09 | Liverpool | | 1-0 | | Bolton | D33 | |||
| h2h | 2006-03-21 | Birmingham City | | 0-7 | | Liverpool | QF |
