He spent one season in the Premier League with Stoke before joining Championship club Sheffield United on loan in 2009, signing permanently in 2010.

He had a short spell as the club's caretaker manager in 2015, and resumed his playing career in non-League football with Tadcaster Albion the following year.

"[16] After a positive start to the season, Cresswell attracted attention from other clubs, with a number of scouts attending matches to watch him play.

[20] He moved to Premier League club Sheffield Wednesday on a four-year contract on 25 March 1999,[6] with the £950,000 fee being the highest received for a York player.

[24][25] Cresswell struggled to establish himself at Wednesday under manager Paul Jewell early in 2000–01,[26] before he resumed playing in the Premier League after signing for Leicester City on 1 September 2000 for a fee of £750,000.

[27] He scored once in 13 appearances for Leicester, his goal coming against former club York in a 3–0 home win in the FA Cup third round on 6 January 2001,[27] having failed to establish himself in the team.

[33] 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.

[37] This helped Preston reach the 2005 Championship play-off final, where they were beaten 1–0 by West Ham United at the Millennium Stadium.

[41] 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.

[41] Having damaged his knee ligaments during the play-off semi-final, Cresswell missed the start of 2006–07,[46] making his first appearance in Leeds' 4–0 home defeat to Stoke City on 14 October 2006.

[47] Cresswell scored in successive matches against Sheffield Wednesday and Luton Town in March 2007, but Leeds were eventually relegated into League One.

[51] Cresswell made 46 appearances for Stoke in 2007–08, scoring 12 goals,[50] as the club won promotion into the Premier League as Championship runners-up.

[56] Having struggled for appearances with Stoke since their promotion into the Premier League, Cresswell joined Championship club Sheffield United on a three-month loan on 29 September 2009 and made his debut the same day as a 76th-minute substitute against Ipswich Town in a 3–3 home draw.

[63][64] The club failed to achieve promotion however, being beaten 8–7 in a penalty shoot-out by Huddersfield Town in the 2012 League One play-off final at Wembley Stadium on 26 May 2012, in which Cresswell was substituted for Chris Porter in the 85th minute.

[65][66] 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.

[68] He played an important role as York fought against relegation,[70] scoring twice in five appearances,[68] before being recalled by new United caretaker manager Chris Morgan on 15 April 2013.

[76] He continued to play for the under-21s after joining Wednesday, and scored his first goal for them in a 3–0 home win over Sweden in a 2000 UEFA European Under-21 Championship qualification match on 4 June 1999.

[76] Cresswell returned to York as a commercial, academy and community development consultant in April 2014, having previously intended to pursue a career in coaching.

[80] He was in charge for the 1–0 away defeat to Crawley Town on 31 October 2015,[81] before ceasing his caretaker duties upon the appointment of Jackie McNamara as manager on 4 November.

[83] He resumed his playing career aged 38 when signing for Northern Counties East League Premier Division club Tadcaster Albion on 7 April 2016.

[88] Cresswell married Zoe Chapman at Christ Church, Bridlington, on 7 June 2003, with former York City teammate Jonathan Greening being his joint best man.

[90] He participated in a 170-mile bike ride during 2012 to raise money for a charity which helps children with Dravet's syndrome, after his twin nieces were diagnosed with the disorder.