York City in 1998 Cresswell started playing for Bridlington Rangers at the age of eight before joining the
York City youth system aged 14 in 1991. Having been top scorer for the Northern Intermediate League team for three consecutive seasons, he signed a professional contract on 15 November 1995. Cresswell admitted he had not made the impact he had hoped to in the York first team, but ahead of 1998–99 said "I've had some stick from a small number of fans, but hopefully I can prove them wrong. I will prove them wrong. This a big season for me. I want to do it for York City. I want to do it for myself."
Manager Alan Little claimed some clubs were making illegal approaches for the player, and that this was having a detrimental effect on his performances.
Preston North End manager
David Moyes claimed his club had a bid of more than £500,000 for Cresswell rejected, while York chairman
Douglas Craig rejected this, saying a formal offer had not been received from any club. He was York's top scorer in 1998–99 with 19 goals from 42 appearances. On his transfer, Cresswell said: "This move is no disrespect to York, it's just that I have always wanted to play at a much bigger club and as high as possible". His debut came in Wednesday's 2–1 home defeat to
Coventry City on 3 April 1999, before scoring his first goal with an 87th-minute winner at home to
Liverpool in a 1–0 win on 8 May.
Leicester City Cresswell struggled to establish himself at Wednesday under manager
Paul Jewell early in
2000–01, before he resumed playing in the Premier League after signing for
Leicester City on 1 September 2000 for a fee of £750,000.
Preston North End Cresswell joined First Division club Preston North End on loan for the remainder of
2000–01 on 10 March 2001 and scored five minutes into his debut, a 2–0 win at home to
Wolverhampton Wanderers (Wolves) on 14 March. Cresswell was Preston's top scorer in his first two permanent seasons with Preston, scoring 15 goals in 44 appearances in
2001–02 and scoring 16 in 46 appearances in
2002–03. He was also named Preston's
Player of the Year for 2001–02. He received the first
red card of his career in Preston's 4–1 defeat away to Coventry on 17 March 2004 after he was judged to have kicked out at opponent player
Calum Davenport, although both managers later admitted
David Healy was the culprit. He scored three goals in 47 appearances in
2003–04. He enjoyed his best goal return in 2004–05, top scoring for Preston with 21 goals in 52 appearances.
Leeds United in 2005 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
promotion with Leeds. 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. 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. making his first appearance in Leeds' 4–0 home defeat to
Stoke City on 14 October 2006. after scoring his first goal of the season in Leeds' 3–0 home win over
Colchester United on 11 November. He made his debut in a 1–0 win at
Cardiff City on 11 August 2007, before scoring in his second appearance with an equaliser during stoppage time of extra time in a 2–2 draw away to Rochdale in the League Cup first round on 14 August, although Stoke lost 4–2 in a
penalty shoot-out. Cresswell made 46 appearances for Stoke in
2007–08, scoring 12 goals, He was regularly used on the
left wing by Stoke manager
Tony Pulis, even though his natural position is as a striker. He was quoted as saying he enjoyed playing as a winger, saying "I do my best, and I am quite a fit lad so I get through quite a bit of mileage". featuring in 34 matches and scoring one goal. finishing
2009–10 as top scorer with 14 goals. He was rewarded with a new three-year contract with the club in June 2010. He scored five goals in 36 appearances in
2010–11 as United were relegated into League One. Towards the end of the transfer window however United agreed a revised deal to change his role to that of
player-coach and as such he would be remaining at
Bramall Lane for the foreseeable future. On his return to the team, Cresswell came on as a substitute and scored a header in United's 5–3 victory over
AFC Bournemouth on 1 September 2012. He marked his second York debut by scoring a 73rd minute
penalty kick on 23 March 2013 away to
Torquay United in a 2–1 defeat. scoring twice in five appearances, In July 2013, new United manager
David Weir stated that Cresswell would be leaving the club, before he signed for York permanently on a one-year contract on 16 July 2013. His first appearance after signing permanently came in the first match of
2013–14, a 1–0 home win over
Northampton Town on 3 August 2013. He made eight appearances for York in 2013–14. ==International career==