Cresswell played poorly in the first half, but had a number of chances on goal during the second half. Cresswell was bought by Preston's Championship rivals Leeds United on a four-year contract on 24 August 2005 for a fee of £1.15 million, after rivals Sheffield United had a £1 million bid accepted. After the signing was completed, manager Kevin Blackwell said "To get a player of Cresswell's quality is amazing", while Cresswell cited his desire to win automatic promotion with Leeds. He first found the net with two goals in Leeds' League Cup 2–0 away victory against Rotherham United on 20 September 2005. However, Cresswell suffered knee ligament damage in a match against Derby County eight days later. This injury kept Cresswell out of action for seven weeks, making his return in Leeds' 1–0 defeat away to Wolves on 17 December 2005, and scoring in his second match back against Coventry City in a 3–1 home win on 26 December. Another knee injury picked up during a training session in February 2006 kept him out of the team until he entered Leeds' 1–1 draw with former club Preston in the Championship play-off semi-final first leg as a 78th-minute substitute on 5 May 2006. However, he was sent off in the 2–0 win in the second leg, meaning he was suspended for the 2006 Championship play-off Final, which Leeds lost 3–0 to Watford at the Millennium Stadium. He finished 2005–06 with 21 appearances and seven goals for Leeds. Having damaged his knee ligaments during the play-off semi-final, Cresswell missed the start of 2006–07, making his first appearance in Leeds' 4–0 home defeat to Stoke City on 14 October 2006. However, he sustained a knee injury in November 2006, after scoring his first goal of the season in Leeds' 3–0 home win over Colchester United on 11 November. His return from injury came as a 68th-minute substitute in a 2–1 victory at home to Crystal Palace on 10 February 2007. Cresswell scored in successive matches against Sheffield Wednesday and Luton Town in March 2007, but Leeds were eventually relegated into League One. He finished the season with four goals in 23 appearances. Leeds were resigned to losing their senior players after going into administration, with Championship club Stoke City signing Cresswell on a three-year contract for an undisclosed fee on 2 August 2007, after Hull City had pulled out of a deal after expressing concerns following his medical.