Dean Whitehead (born 12 January 1982) is an English football coach and former professional footballer who is the assistant manager of EFL League Two club Tranmere Rovers. A midfielder who occasionally played as a right-back, he made 622 league and cup appearances in a 19-year playing career, scoring 29 goals.
Whitehead joined his local non-League club Abingdon Town before he signed for Football League club Oxford United in 1999. He played for Oxford in the Second Division until their relegation into the Third Division in 2001. He 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 get promoted from the Championship in 2017 before retiring in 2018.
He has coached at Huddersfield Town, Shrewsbury Town, Port Vale, Beşiktaş (Turkey), Cardiff City, Watford, Barnsley, Stoke City, Blackburn Rovers, and Tranmere Rovers.
Born in Abingdon, Oxfordshire, Whitehead started his career with Abingdon Town's youth team, before joining the youth scheme of his local professional Football League club, Oxford United as an apprentice.
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's 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.
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.
In the 2001–02 season, Whitehead 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 to criticism by manager Ian Atkins for unprofessionalism over refusing to do the club's fitness programme, which were denied by the pair, who stated the whole thing was a misunderstanding. Towards the end of the 2001–02 season, he began playing in a central midfield role. Despite missing out three matches, he played in 43 fixtures as Oxford United had a poor season, finishing in 21st position.
Whitehead began the 2002–03 season as a first-team regular in good form. At the beginning of November, Whitehead's performances against Aston Villa and Rochdale were praised by Atkins. He continued with his impressive displays to the end of the year. Whitehead later scored his first goal of the season on 26 December, in a 3–0 win over AFC Bournemouth. However, he found his first-team chances 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 2003–04 season, Whitehead reclaimed his place in the team following the departure of Dave Savage. On 27 September 2003, he scored his first goal of the season, in a 3–0 win over Northampton Town. He was praised for his performances in his run of first-team football. Whitehead scored his first brace of the season on 18 October, in a 4–0 win over Bury. He also scored a free kick on 1 November, helping his team 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 at the Kassam Stadium until 2006. On 21 February 2004, he scored against Bury for the second time that season, in a 1–1 draw. In a 2–1 loss against Macclesfield Town on 1 May, Whitehead captained the side for the first time, in the absence of Andy Crosby. By the end of the 2003–04 season, he made 47 appearances and scoring seven goals. Whitehead was named the club's Player of the Season.
After playing for the club for five seasons, his contract expired and he turned down the offer of a new one from the club. Manager Graham Rix revealed that Whitehead would have been appointed as Crosby's successor as captain if he signed a new contract with the club.
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 desire to play at a higher level was why he joined 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. He quickly became a key member of the team, playing regularly despite facing competition from other midfielders. His run in the first-team saw him praised by manager Mick McCarthy. On 25 October 2004, 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, in a 2–0 win over Cardiff City. Whitehead scored three more goals later in the season in games that ended up as 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 times in all competitions. He helped Sunderland to win the Championship in 2004–05, and was chosen as Players' Player of the Year by his teammates at the end of the season.
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 made a positive impact for the side. His performances earned him comparison to Manchester United's Roy Keane. On 29 October 2005, he scored his first Premier League goal, in a 4–1 loss against Portsmouth. Three weeks later, on 19 November, 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, a more unfamiliar role. On 26 November, Whitehead signed a contract extension with the club, keeping him at the Stadium of Light until 2010. He scored a swerving 30 yards (27 m) free kick past then-England goalkeeper Paul Robinson in a 3–2 defeat against Tottenham Hotspur at White Hart Lane on 3 December. Sunderland were eventually relegated to the Championship for the 2006–07 season. Despite missing out one match during the 2005–06 season, Whitehead went on to make thirty–eight appearances and scored three goals in all competitions.
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. He continued to establish himself in the first-team, under the management of newly appointed manager Roy Keane. Whitehead then scored his first goal of the season against West Bromwich Albion, in a 2–0 win during which he was named as man of the match. Then, on 21 October, he scored his second goal of the season, in a 2–0 win against Barnsley. During the 2006–07 season, Whitehead resigned the captaincy to concentrate on his football but he deputised for the frequently injured Steven Caldwell and was reappointed as captain on a permanent basis after Caldwell was sold to Burnley. At one point during the 2006–07 season, Whitehead played in a right–back position following the absence of Nyron Nosworthy. The following month, he reverted 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–seven appearances and scoring four times in all competitions.