He spent four seasons at Spotland, playing 188 league and cup matches and being named Player of the Year before joining Macclesfield Town in July 2003.
He moved on to Bury in February 2004, where he featured in another 108 first-team games and was named Player of the Year for the 2005–06 season before signing with Hyde United of the Conference North in November 2006.
Born in Bolton, Lancashire,[2] Flitcroft spent time as a child with Manchester City before he began an apprenticeship with Preston North End at the age of 14.
[7][8][9] Flitcroft scored six goals in 34 games during the 1996–97 season, as Chester reached play-offs, though lost out to Swansea City at the semi-final stage.
[20] Flitcroft signed a two-year contract with Macclesfield Town on 9 July 2003 and was immediately installed as captain at Moss Rose.
[21] He played 15 Third Division games for the "Silkmen" before losing his first-team place when John Askey replaced David Moss as manager in October.
[25][24] He scored his first goal for the club in a 4–0 win over Kidderminster Harriers at Gigg Lane on 30 August 2004, though was sent off later in the match after picking up a second yellow card.
[30][31] He was named as the club's Player of the Year for what the Bury Times described "his wholehearted and consistent displays in the Shakers' engine room".
[33] He left Bury, his last professional club as a player, in November 2006 after falling out of favour with manager Chris Casper and admitted it was "a massive wrench" to leave, saying that he had been focusing too much on mentoring youngsters during the 2006–07 season and had neglected his own performances.
[34] Flitcroft joined Conference North club Hyde United and made his debut for the "Tigers" in the FA Trophy on 28 November 2006, playing "a superb game" in a 3–0 win at Chasetown.
[35] He made his home debut at Ewen Fields on 9 December, picking up an assist for Paul Gedman's equalising goal in a 1–1 draw with Scarborough.
[5] His limited skill set meant he rarely featured above the fourth tier, though his work rate and consistency kept him in the professional game.
[43] He said "Hilly getting sacked... really floored me" and that he had intended to leave but Hill persuaded him to stay on as caretaker as the two men remained close friends.
[52] Flitcroft guided Barnsley to Championship safety on the final game of the 2012–13 season with a 2–2 draw at Huddersfield Town and stated that it was "Mission Impossible achieved".
[59] In the January transfer window he released five players – Gareth Roberts, Shaun Harrad, Marlon Jackson, Euan Holden and Jessy Reindorf, and renovated the defence by signing Pablo Mills, Robbie McIntyre, James Burke, Frédéric Veseli and Jim McNulty.
[62] Bury enjoyed a positive start to their promotion campaign, though Flitcroft said that "I don't know who thinks we're going to win every game this season.
In preparation for the 2016–17 campaign, Flitcroft released six players and brought in a number of new signings, including: Antony Kay, Greg Leigh, Leon Barnett, Neil Danns, Paul Rachubka, Chris Brown and James Vaughan.
[70] On 16 November, Flitcroft was sacked after a run of 11 games without a win that coincided with a series of injuries to first-team players such as Tom Pope, Danny Mayor and Nathan Cameron.
[71][72] Gareth Southgate's promotion to England manager left a vacancy for the head coach role of the under-21 team and Flitcroft applied for the position, making into the final four of the interview process, though the job instead went to Aidy Boothroyd.
"On 5 June 2017, Flitcroft was appointed as manager of Swindon Town, who had sacked Luke Williams following the club's relegation into League Two.
[74][75] A club statement said that: "David has been given a very competitive budget and will now begin the job of putting a squad together with the aim of competing at the top of League Two.
"[76] In the summer transfer window he signed goalkeeper Reice Charles-Cook; defenders Olly Lancashire, Ben Purkiss, Chris Robertson and Kyle Knoyle; midfielders James Dunne, Matthew Taylor and Amine Linganzi; and forwards Paul Mullin, Donal McDermott and Kaiyne Woolery.
[77] He further strengthened his front line in the January transfer window by bringing in Marc Richards and Keshi Anderson (who was already at the County Ground on loan).
[78][79] The "Robins" were seventh in the table when Flitcroft was appointed as manager at League Two promotion rivals Mansfield Town on 1 March 2018, who paid Swindon a compensation package to secure his release.
[89] On 31 August 2019, Flitcroft was named assistant to new manager Keith Hill at his hometown team, Bolton Wanderers, the duo working together once again after spells together at both Rochdale and Barnsley.
[93] Flitcroft told the press that his targets would be to appoint a manager, improve player recruitment and to ensure the playing squad suffered less injuries.
[94] Darrell Clarke was appointed as manager seven days later and the club paid Walsall a compensation fee to sign him.
[92] Clarke and Flitcroft recruited 12 players for the start of the 2021–22 season: goalkeepers Lucas Covolan and Aidan Stone; defenders Lewis Cass, Ryan Johnson, Aaron Martin, Dan Jones and Mal Benning; midfielders Ben Garrity, Brad Walker and Tom Pett; and strikers Jamie Proctor and James Wilson.
[97] He helped to oversee seven permanent signings and six loan singings to prepare the club for League One in the 2022–23 season, whilst six first-team players were moved on.