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Following his retirement, Whitehead took up a coaching role at Huddersfield Town as part of David Wagner's First Team technical staff, having earned a UEFA A coaching license, and is expected to take charge of the Club's new Under-17 Academy age group from 1 January 2019. By October, he took charge for Huddersfield Town's Under-17s side.

On 16 November 2019, Whitehead joined Sam Ricketts' backroom staff at League One side Shrewsbury Town, replacing Joe Parkinson as first-team coach.

Ahead of the 2017–18 season, on 6 July 2017, Huddersfield announced that Whitehead had extended his contract with the club until the end of the 2017–18 Premier League season with manager David Wagner stating: "Even if he plays less for us, he is still a very important part of the team and our dressing room." He was included for the 25-man squad for the Premier League. He made his first appearance of the 2017–18 season, where he started the whole game, in a 2–1 win over Rotherham United in the second round of the League Cup on 23 August 2017. Then, on 30 September 2017, Whitehead made his first Premier League appearance – his first in four years – as a late substitute, in a 4–0 loss against Tottenham Hotspur. However, his first team at Huddersfield Town continued to be restricted on the substitute bench for the most of the 2017–18 season. On 11 May 2018, Whitehead announced his retirement from professional football at the end of the 2017–18 season. He made his last appearance for the club (and his football career), coming on as a late substitute, in a 1–0 loss against Arsenal on the last game of the season.

Ahead of the 2016–17 season, Whitehead turned down a move to Rotherham United and said he would fight for his place in the first team. He missed the first two matches of the season for suspension over involving an incident against Brentford on the last game of the season. He made his first appearance of the season on 20 August 2016, where he started the whole game, in a 2–1 win over Barnsley. However, Whitehead struggled in the first team under David Wagner, due to strong competitions from other midfielders. He captained the side for the first time this season, in a 2–1 win over Rotherham United on 27 September 2016. Due to Hudson's absent, Whitehead often stand in as captain, though Tommy Smith was another stand in captain when he was not included in the starting eleven. Throughout the January transfer window, he stayed at the club after being linked with a move to Wigan Athletic. However, in a 1–0 loss against Burton Albion on 1 April 2017, he was sent–off for a second bookable offence. Whitehead was later featured three times as an unused substitute bench in the Championship Play–Offs, as he was part of the squad that saw Huddersfield side promoted to the Premier League after beating Reading 5–4 in penalty shoot–out after a 0–0 in the EFL Championship play-off Final. At the end of the 2016–17 season, he went on to make twenty appearances in all competitions.

In June 2015, Whitehead signed for Championship club Huddersfield Town on a two-year contract. Upon joining the club, he was given a number four shirt ahead of the 2015–16 season.

He made his debut for in a 2–0 defeat against Hull City at the KC Stadium on 8 August 2015. This was followed by captaining Huddersfield Town for the first time on 11 August 2015, in a 2–1 loss against Notts County. Since the start of the season, Whitehead quickly established himself in the first team, under the management of Chris Powell. He captained the side once again following an absent of Mark Hudson for five matches between 12 September 2015 and 3 October 2015. Whitehead's performance saw him earned BWF Player of the Month for October and November. However, he suffered a knee injury during a 2–0 win over Birmingham City on 5 December 2014 and was sidelined for two months. A month later, on 23 January 2016, Whitehead returned to the first team from injury, coming on as a late substitute, in a 2–1 loss against Brighton & Hove Albion. Since returning to the first team, he regained his first team place in the starting eleven for the rest of the season. At the end of the 2015–16 season, Whitehead went on to make thirty–six appearances in all competitions

In August 2015, Whitehead appeared in court, charged for speeding at M62. After having his court adjourned twice, he already has nine points on his driving licence and another three would automatically trigger a disqualification.

In the 2014–15 season, Whitehead continued to feature in the first team at the start of the season, mostly coming on as a substitute. This was due to facing competitions for a defensive midfield position with Richard Smallwood, Grant Leadbitter and Adam Clayton. However, in a 4–0 win over Brentford on 20 September 2014, he was sent–off "for an over the top tackle on Judge", leading the referee giving him "a straight red card." After serving a three match suspension, he returned to the first team from suspension, coming on as a late substitute, in a 2–0 win over Fulham on 2 October 2014. Whitehead captained the side for the first time in the league, in a 1–1 draw against Watford on 25 October 2014. His first time as captain of the season came on 25 August 2014, in a 3–1 win over Preston North End. However, throughout the 2014–15 season, Whitehead was demoted to the substitute bench. But he does feature cover, playing twice as a right–back position and six times a centre–midfield. He also captained the side once again this season against Sheffield Wednesday on 28 February 2015, which saw Middlesbrough lost 2–0. In the Championship play-offs, Whitehead was featured three times as a right–back, including the 2015 Championship play-off Final at Wembley Stadium, where they lost 2–0 to Norwich City. Despite this, Whitehead went on to make twenty–five appearances in all competitions.

Whitehead signed for Championship club Middlesbrough on 2 July 2013 on a two-year contract. Manager Tony Mowbray revealed that Whitehead's experience of gaining promotion from the Championship twice was the key reason in signing him. Upon joining the club, he was given a number eighteen shirt ahead of a new season.

Whitehead made his Middlesbrough debut, where he started the whole game, in a 2–1 loss against Leicester City in the opening game of the season. Since joining the club, he quickly established himself in the starting eleven in the midfield position. Despite being in the first team, Whitehead faced strong competitions from other midfielders over the position. After missing four matches between late–October and late–November, he returned as a late substitute on 30 November 2013, in a 1–0 win over Bolton Wanderers. Whitehead scored his first and what turned out to be only goal for the club in a 2–1 loss away to Derby County on 4 December 2013. Two weeks later, on 21 December 2013, he captained Middlesbrough for the first time, in a 2–0 win over Millwall. Later in the 2013–14 season, Whitehead was suspended on three occasions, including being sent–off for dissent, in a 1–0 loss against Sheffield Wednesday on 1 March 2014. Despite this, he remained in the first team, where he captained the side four more times later in the season. Whitehead played 38 times and scoring once in the 2013–14 season, as Middlesbrough finished in 12th position.

Ahead of the 2011–12 season, Whitehead said that he's expecting to face new competitions in the club's midfield section. He then made his 100th appearance for Stoke on 3 November 2011 in a UEFA Europa League match against Maccabi Tel Aviv, scoring the first goal in a 2–1 victory. He played in 10 of Stoke's 12 European fixtures in 2011–12, and ended the season having played in 47 matches in total. He made a bad start to 2012–13, as on the opening day of the season away to Reading he conceded a 90th-minute penalty and was sent off after picking up a second yellow card. He remained back-up to Glenn Whelan for the remainder of the season being used mainly as a substitute, although he was assigned as a stand-in right back in absent of Andy Wilkinson and Ryan Shotton. He was released by Stoke at the end of 2012–13.

His first Premier League goal for Stoke came against Birmingham City on 9 November 2010 with Whitehead scoring the winning goal in a 3–2 win. He scored his second league goal for Stoke away to Manchester United on 4 January 2011, becoming the first Stoke player to score at Old Trafford since 1980. Towards the end of 2010–11, Whitehead lost his place in the starting eleven to a resurgent Glenn Whelan, making a number of cameo appearances from the bench. One of these came in the 2011 FA Cup Final against Manchester City.

Whitehead signed a four-year contract with Premier League club Stoke City on 24 July 2009 for an initial £3 million fee, rising to £5 million with add-ons. He stated that Stoke's team spirit was the main reason for his move to the club.

He made his debut on 15 August 2009 in a 2–0 win over Burnley. Whitehead made a slow start to his Stoke career with a number of anonymous performances. However, following a 0–0 draw with Blackburn Rovers, he earned praise from manager Tony Pulis. Whitehead scored his first goal for Stoke when he converted winger Matthew Etherington's cross in the 86th minute in a 3–1 FA Cup fourth-round win over Arsenal on 24 January 2010. Whitehead was sent off by Mike Dean against Tottenham Hotspur in March 2010 a decision which drew heavy criticism from Tony Pulis and Matthew Etherington.

Ahead of the 2008–09 season, Whitehead was linked a move away from Sunderland, as newly promoted Premier League side Stoke City made a £3 million bid on him. In response, he stated that he wanted to stay at the club. At the start of the season, Whitehead continued to remain in the starting line-up for the side. After a 4–1 loss against Bolton Wanderers on 29 November 2008, he was heavily booed by the club's supporters for the performance throughout the match, in what turns out to be Keane's last match as the Sunderland Manager. He continued to be linked away from Sunderland throughout the January transfer window. Despite missing out four matches during the season, Whitehead helped the side avoid relegation once again after losing 3–2 to Chelsea on the last game of the season but defeats for Newcastle and Middlesbrough meant Sunderland were safe. At the end of the 2008–09 season, Whitehead went on to make thirty–eight appearances in all competitions. He left Sunderland in August 2009 after making 200 appearances for the club.

In the 2007–08 season, Whitehead started out the season, playing in the right–back position against Tottenham Hotspur in the opening game of the season before sustaining a cruciate knee ligament injury in a match against Wigan Athletic in August 2007, which ruled him out for six months. He made his comeback from injury in early–November 2007 and made his first team return on 24 November 2007, where he started the whole game, in a 7–1 loss against Everton. Since returning from injury, he regained back his first team place for Sunderland throughout the season. He then scored his first goal of the season, in a 2–1 loss against Manchester City on 14 April 2008. At the end of the 2007–08 season, Whitehead helped Sunderland successfully avoided relegation by three points. Despite being sidelined during the season, Whitehead went on to make twenty–eight appearances and scoring once in all competitions. During towards before and after the end of the season, Whitehead found himself playing at right-back, although this ended when Whitehead moved back into central midfield.

Ahead of the 2006–07 season, Reading had a bid of £1.2 million for Whitehead rejected in July 2006. The following month, Whitehead and teammate Liam Lawrence both signed new contracts in August 2006. He continued to establish himself in the first team, under a new management of Roy Keane. Whitehead then scored his first goal of the season against West Bromwich Albion, in a 2–0 win to give the club's first win of the season and was named Man of the Match. Then, on 21 October 2006, he scored his second goal of the season, in a 2–0 win against Barnsley. During 2006–07 season, Whitehead resigned the captaincy to concentrate on his football but he deputised for the frequently injured Steven Caldwell and was appointed on a permanent basis after Caldwell was sold to Burnley and was eventually given the captain's armband for the second time. At one point during the 2006–07 season, Whitehead played in a right–back position following an absent of Nyron Nosworthy. The following month, he reverted back to his central midfield position. Towards the end of the season, Whitehead scored two more goals. Sunderland finished first in the Championship in 2006–07, thus making an instant return to the Premier League. At the end of the 2006–07 season, Whitehead was included in the PFA Team of the Year. He also came second in the club's Player of the Year vote. Despite being sidelined during the 2006–07 season, Whitehead went on to make forty–six appearances and scoring four times in all competitions.

In the 2005–06, Whitehead continued to establish himself in the starting eleven, with the club playing in the Premier League. Despite the club's struggles in the Premier League at the start of the season, he was one of the bright spot to make an impact for the side. His performance earned him comparison to Manchester United's Roy Keane. It wasn't until on 29 October 2005 when he scored his first Premier League goal, in a 4–1 loss against Portsmouth. Three weeks later, on 19 November 2005, Whitehead scored his second goal of the season, in a 3–1 loss against Aston Villa. By November, he began playing in the right–wing position in an unfamiliar role. On 26 November 2005, Whitehead signed a contract extension with the club, keeping him until 2010. He scored a swerving 30-yard free kick past then England goalkeeper Paul Robinson in a 3–2 defeat against Tottenham Hotspur at White Hart Lane on 3 December 2005. Sunderland were eventually relegated to the Championship for 2006–07 season. Despite missing out one match during the season, Whitehead went on to make thirty–eight appearances and scoring three times in all competitions.

In June 2004, Whitehead signed for Championship club Sunderland on a free transfer. Upon signing a three–year contract with the club, he revealed that his ambition and desired to play at a higher level was the reason of joining Sunderland. Sunderland were ordered to pay £150,000 to Oxford at an FA tribunal, to compensate for the time and money put into his development. Oxford would also receive 25% of any fee should Sunderland sell Whitehead.

Whitehead made his Sunderland debut, coming on as a late substitute for Ben Clark, in a 2–0 loss against Coventry City in the opening game of the season. Since joining the club, he quickly became a key member of the team, playing in the midfield position despite facing competitions from other midfielders. His run in the first team saw him praised by Manager Mick McCarthy. It wasn't until on 25 October 2004 when he scored his first goal for the club, in a 1–0 win over Rotherham United. He then scored his second goal of the season on 11 December 2004, in a 2–0 win over Cardiff City. Whitehead scored three more goals later in the season that ended up with Sunderland victories. Following his good performance at Sunderland halfway through the season, he was given a new three-year contract during 2004–05. Despite missing out three matches during the season, as he went on to make forty–three appearances and scoring five rimes in all competitions, he helped Sunderland won the Championship in 2004–05, and was chosen as Players' Player of the Year by his teammates at the end of the season.

In 2003–04 season, Whitehead reclaimed his place in the team following the departure of Dave Savage. It wasn't until on 27 September 2003 when he scored his first goal of the season, in a 3–0 win over Northampton Town. His run of the his first team football was praised, due to his good performance. Whitehead scored his first brace of the season on 18 October 2003, in a 4–0 win over Bury. He also scored a free kick on 1 November 2003, to make a 3–1 comeback win over Darlington. As a result, he was offered a two–year contract by the club, which would keep him until 2006. On 21 February 2004 against Bury for the second time this season, he scored against them once again, in a 1–1 draw. In a 2–1 loss against Macclesfield Town on 1 May 2004, Whitehead captained the side for the first time in absent of Andy Crosby, who was absent from the first team squad. At the end of the 2003–04 season, he made 47 appearances and scoring seven goals. For his performance, Whitehead was named the club's Player of the Season.

In the 2002–03 season, Whitehead started the season well when he received a handful of first team football for the side. At the beginning of November, Whitehead's performance against Aston Villa and Rochdale was praised by Manager Atkins. He continued with his display by the end of the year. Whitehead later scored his first goal of the season on 26 December 2002, in a 3–0 win over Bournemouth. However, towards the end of the 2002–03 season, he found his first team place limited between January and March. As a result, he was restricted to 22 appearances in 2002–03 as Oxford missed out on a play-off place by a single point.

In the 2001–02 season, Whithead scored his first goal in the Football League against Rushden & Diamonds on 31 August 2001. He was soon a first team regular in 2001–02 season, establishing himself in the midfield position. However, halfway through the season, Whitehead, along with Chris Hackett were subjected of criticism by Manager Ian Atkins for unprofessionalism over refusing to do the fitness programme, which were denied by the pair, who stated this whole thing was a misunderstanding. Towards the end of the 2001–02 season, he began playing into a central midfield position. Despite missing out three matches, he played in 43 fixtures as Oxford United had a poor season, finishing in 21st position.

In the 2000–01 season, Whitehead soon received a handful of first team appearances for the club by Manager Denis Smith. Although he received his first team opportunities, he found himself in a competition with Matt Murphy and other midfielders for the central role. Despite being sidelined on two occasions, due to suspensions, Whitehead played in 23 matches in 2000–01 season, as Oxford suffered relegation to the Third Division. At the end of the 2000–01 season, he signed a long–term contract with the club.

Whitehead joined his local non-League club Abingdon Town before he signed for Football League club Oxford United in 1999. He impressed in the lower divisions and was signed by Championship club Sunderland in 2004. He won promotion in his first season with Sunderland, although they were relegated from the Premier League after one season. He was made captain by Roy Keane as Sunderland claimed an instant return to the top flight. After two more seasons in the north-east, Whitehead signed for Stoke City in 2009. He helped Stoke reach the 2011 FA Cup Final, where the team finished runners-up to Manchester City. After spending four seasons with Stoke, Whitehead signed for Middlesbrough in 2013. He moved to Huddersfield Town two years later, helping them to promotion from the Championship in 2017 before retiring in 2018.

He progressed through the ranks, making his first-team debut in a 2–0 win over Luton Town in the Football League Trophy on 7 December 1999. This turned out to be Whitehead only appearance of the 1999–00 season, as he spent the rest of the season on the substitute bench. At the end of the 1999–00 season, he signed a contract with the club.

Dean Whitehead (born 12 January 1982) is an English former professional footballer who played as a midfielder and occasionally at right-back. He is currently first team coach at League One club Shrewsbury Town.