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After huge speculation, on 14 June 2019, Woodgate was appointed as the new permanent manager of Middlesbrough, signing onto a three-year contract. He brought in former associates Robbie Keane and Leo Percovich as his assistants, whereas Danny Coyne was appointed as the club's new goalkeeping coach. Following his appointment, Woodgate stated that he wanted to reintroduce attacking football to the club, having informed club chairman Steve Gibson that he wanted to "play a more expansive game", with both parties wanting to redevelop the team's style of play after Pulis' controversial spell.

After an indifferent start to management, Middlesbrough supporters demanded for Woodgate to be sacked, with many doubting his side's ability to avoid relegation. With pressure mounting on Woodgate, tabloids alleged that former Cardiff City and highly-experienced Premier League manager Neil Warnock was favoured to replace him, causing chairman Gibson to openly state that he "is really behind" the manager, with him "understanding January needs" to improve the team. December, however, was a positive month for Middlesbrough; recording four victories as well as a singular draw and defeat. Crucial victories over Charlton Athletic, Stoke City, Huddersfield Town and then-league leaders West Bromwich Albion, a draw over Nottingham Forest and defeat to Swansea City saw them rise up to sixteenth in the Championship table, finishing off 2019 nine points above the relegation zone. As a result of Middlesbrough's turn around in form, Woodgate was rewarded as being named the Championship Manager of the Month for December.

After a brief spell as an international scout for Liverpool in Spain and Portugal, on 31 March 2017, Woodgate was appointed as an assistant coach to newly-appointed Middlesbrough caretaker manager Steve Agnew, following the dismissal of Aitor Karanka, with Woodgate becoming one of three new arrivals in the club's coaching staff alongside fellow part-timers Joe Jordan and Paul Jenkins. After the club were relegated from the Premier League at the end of the season, Woodgate vacated his position after new manager Garry Monk brought in his own coaching staff, with him being replaced by James Beattie.

Following his departure from the first team, Woodgate joined the club's Academy coaching staff in June 2017, as the under-18 team's assistant coach under Mark Tinkler. In December 2017, Woodgate returned to his previous position as first team assistant coach, under the management of Tony Pulis, who replaced a dismissed Monk. In May 2019, Woodgate was the only member of Pulis' coaching staff not to be relieved from his duties, which saw him become the frontrunner to succeed the Welshman.

On 10 February 2015, Woodgate started a match for Middlesbrough for the first time in 6 months and scored the first goal in a 2–1 win against Blackpool which sent Boro to the top of the Championship table. He was an unused substitute on 25 May as they lost the play-off final to Norwich City at Wembley. On 16 July 2015, Woodgate signed a one-year extension despite previously announcing retirement as a player. After playing only one game in the 2015–16 season, Woodgate left Middlesbrough on the expiration of his contract in May 2016 and retired from football.

The summer transfer window saw the Smoggies complete the signings of former club goalkeeper Tomás Mejías, Marcus Browne, Marc Bola and Anfernee Dijksteel. Woodgate's first game as a manager came on 2 August, a 3–3 draw against newly-promoted Luton Town, which saw supporters criticise his side's defence. At the end of August, Middlesbrough sat eighteenth in the Championship, having recorded a single victory out of a possible six as well as collecting three draws and two defeats. Middlesbrough slipped into the relegation zone following a goalless draw against Fulham, remaining there for a further two matches until a 2–2 draw with Hull City saw them climb into twenty-first, only qualifying for a higher league position through goal difference.

During the winter transfer window, Middlesbrough were heavily active: Patrick Roberts, Lukas Nmecha, Ravel Morrison and Harold Moukoudi all arrived on loan, whereas Dejan Stojanović joined for an undisclosed fee from St. Gallen. Woodgate was criticised by supporters when reigning Player of the Year Darren Randolph left to return to West Ham United, which resulted in Aynsley Pears settling himself as first-choice goalkeeper. Middlesbrough dipped in form resulting in Woodgate's side heavily dropping down the league table; a 1–0 defeat to Yorkshire rivals Leeds United saw Middlesbrough drop to twenty-first, tying on points with Wigan Athletic, the latter looming in the relegation zone. After this, supporters once again demanded for Woodgate to be sacked; the manager later assured unsettled supporters that Gibson continued to "back him" despite their frequent dip in form.

Despite a decent enough start to his Stoke career he went on to have poor performances against Sunderland, Newcastle and Bolton and he was dropped by Pulis and Woodgate admitted that he needs to up his game. He failed to improve much and in a match against Wolverhampton Wanderers Woodgate started the match at right back and struggled against Matt Jarvis and gave away a penalty he was then substituted after twenty minutes by Pulis. He continued to play at right back though and Woodgate admitted that his performances at Stoke have been 'up and down'. His contract with Stoke expired on 30 June 2012 and despite being offered a new deal he chose to return to his former club, Middlesbrough.

Woodgate re-joined his hometown club Middlesbrough on 6 July 2012, signing a three-year contract. He made his second debut for Boro against Bury in the League Cup on 11 August. Woodgate scored his first goal for Middlesbrough in a 4–1 victory against Charlton Athletic on 3 November.

On 19 January 2011, Woodgate played his first game in 14 months in a friendly match with QPR. The defender completed 45 minutes in a 9–2 victory at Spurs Lodge. Following this, on 15 February, a Champions League tie with AC Milan, he came on in the 59th minute for the injured Vedran Ćorluka. He played out the rest of the game; however, was later diagnosed with a strain to his left adductor muscle. Spurs were unsuccessful in persuading Woodgate to agree a pay-as-you-play deal, and he was released on 16 June 2011.

Woodgate signed a one-year contract on a pay-as-you-play deal with Stoke City on 11 July 2011, with a view of a further year on his contract, if he proves his fitness. Following his move to Stoke, Woodgate stated that he wants to get his career back on track. He also revealed that he turned down a number of other contract offers from different clubs. He made his debut in a Stoke City shirt in a pre-season friendly against Aldershot Town, playing for 62 minutes. He made his full debut for Stoke in a 1–0 win over Hajduk Split in the UEFA Europa League he played the full 90 minutes. He then completed his first full 90 in the Premier League for Stoke in a 0–0 draw with Chelsea. Woodgate was left out of Stoke's Europa League squad by manager Tony Pulis who feared a recurrence of Woodgate's injuries if he spent too long travelling.

He went on to play 14 times for them before joining his hometown club Middlesbrough on loan, then permanently for a fee of £7 million. He joined Tottenham Hotspur for £8 million in 2008. He scored the winning goal for Spurs in the League Cup Final against Chelsea and went on to play 44 times in the 2008–09 season. After more injury problems, he only made four appearances in the next two seasons and was released in 2011 and signed on a pay-as-you-play deal with Stoke City. He spent the 2011–12 season at Stoke and after his contract expired re-signed for Middlesbrough, remaining there until his retirement in 2016.

After rejecting the chance to re-sign for Newcastle, Woodgate moved to Tottenham Hotspur for a reported fee of £8 million on 28 January 2008. He made his Tottenham debut against Everton two days later and scored his first Tottenham goal on 24 February 2008 which was a header in the League Cup final against Chelsea in extra-time to win Tottenham their first trophy since 1999. His performance won him the Man of the match award. Woodgate scored his first Spurs league goal on 19 March 2008, coincidentally also against Chelsea, in a 4–4 draw at White Hart Lane. He first captained Tottenham in a 2–1 defeat at White Hart Lane to Aston Villa on 15 September. Following Harry Redknapp's appointment, Woodgate became the second vice-captain, behind Robbie Keane.

On Spurs' disastrous start to the 2008–09 season, Woodgate told the press that it was worse than when Leeds were relegated. Woodgate had been transferred to Newcastle United some 16 months before Leeds's eventual relegation at the end of 2003–04. Woodgate played just three times in Spurs highly successful 2009–10 campaign after succumbing to a long term groin injury. Harry Redknapp hinted at Woodgate's exit due to having to comply with new Premier League rules which limited squad sizes to 25 – ironically these rules were put in place in order to help the careers of English and Welsh footballers. Woodgate travelled to Australia to have surgery.

In July 2007, Woodgate was voted the worst signing of the 21st century by users of the website of Spain's leading sports daily, Marca, polling 37.11% of the votes cast.

In October 2007 he was crowned North East Player of the Year by the Prince's Trust, beating players from Newcastle and Sunderland. During the 2007–08 pre-season Woodgate suffered an injury that allowed fellow hometown defender David Wheater to start in his place during pre-season. Wheater's form in pre-season earned him a place in the starting XI for the opening day Premier League fixture – Wheater's form then continued which triggered the transfer of Woodgate to Tottenham Hotspur.

After almost three years without an international cap, England manager Steve McClaren recalled Woodgate to the squad for the friendly against Spain in February 2007. On 7 February, Woodgate started in the 1-0 defeat at Old Trafford, before being replaced by Jamie Carragher in the 65th minute. The following month, he retained his place in the squad for the Euro 2008 qualifiers against Israel and Andorra. He would go on to miss both games because of a knee injury. In early 2008, Woodgate was named in Fabio Capello's first two England squads, for the friendlies against Switzerland and France, but failed to feature in either game. In May 2008, Woodgate was named in the England squad for the end-of-season friendlies against USA and Trinidad and Tobago. He was an unused substitute in the 2-0 win against USA, before winning his seventh cap in the 3-0 win against Trinidad and Tobago. On 20 August, Woodgate won his eighth and last cap in the friendly against Czech Republic, he replaced Rio Ferdinand in the 58th minute of the 2-2 draw at Wembley Stadium.

By February 2006, Woodgate had established himself as a first team player, with the other centre half position rotating among Sergio Ramos, Iván Helguera, Francisco Pavon and Álvaro Mejía. One Spanish newspaper even described him as having "become Madrid's true leader". However, further injury setbacks again stopped him playing. He was considered to have an outside chance of making the England squad for the 2006 FIFA World Cup, but due to surgery on his back was not named in the squad.

On 30 August 2006, Woodgate signed a one-year loan move to hometown club Middlesbrough. He made his debut against Arsenal at The Emirates Stadium on 9 September. He was later voted man of the match by local radio station, Century FM. In April 2007 Middlesbrough announced Woodgate would be their first summer signing for a fee of £7 million. He signed a four-year contract, keeping him at the club until June 2011.

Woodgate did not make any appearances for Real Madrid in his first season in Spain, eventually making his debut on 22 September 2005, in a league match against Athletic Bilbao. The game did not go well for him, as he scored an own goal and was later sent off for a second bookable offence. He scored his only goal for Real Madrid by heading the equaliser in the 4–1 UEFA Champions League defeat of Rosenborg BK on 19 October, his first appearance for the club in European competition.

Woodgate signed for Real Madrid in August 2004 for a transfer fee of £13.4 million. This was to the surprise of many in the football world, due to his frequent absences through injury at his previous clubs, and indeed he was injured at the time of the transfer.

Woodgate started his career at Leeds United. He was sold to Newcastle United for £9 million in 2003, where he impressed despite injury problems. His performances in Europe for Newcastle led to Real Madrid signing him for £13.4 million in 2004. Injuries blighted his time in Madrid and he failed to make a single appearance in the entire 2004–05 season. On his debut for Real Madrid, he scored an own goal and was sent off for two bookable offences.

Woodgate signed for Newcastle United in January 2003 for £9 million with add ons. He impressed and quickly became a fan favourite. One of his finest games came in Newcastle's 2004 UEFA Cup semi final clash with Olympique de Marseille, completely nullifying the threat of their forward line and clinical forward Didier Drogba. Unfortunately for Newcastle, a serious injury saw him end his final season early, and could not feature in the second leg, where Newcastle were defeated 2–0 and knocked out.

On 2 September 2002, manager Sven-Göran Eriksson recalled Woodgate to the England squad for the friendly against Portugal. He went on to earn his second cap, replacing Rio Ferdinand at half-time in the 1-1 draw at Villa Park. Woodgate was called up for the Euro 2004 qualifiers against Slovakia and Macedonia in October 2002, he started and played the whole 90 minutes in both games. Injuries blighted Woodgate over the next couple of years, but he did manage to win his fifth cap in a friendly against Sweden on 31 March 2004. He started the 1-0 defeat at Ullevi in Gothenburg, and was replaced by Anthony Gardner at half-time. A thigh injury picked up whilst playing for Newcastle United, in April 2004, ruled Woodgate out of the Euro 2004 tournament in Portugal.

In 2000, he was a defendant with teammate Lee Bowyer in a Crown Court trial due to his involvement in an incident outside the Majestyk nightclub in Leeds, in which a student suffered severe injuries. The initial trial collapsed, and following a second trial, in December 2001, Bowyer was cleared of charges of grievous bodily harm with intent and affray, while Woodgate was convicted of affray and sentenced to 100 hours' community service. He was also banned from international selection by the Football Association, which prevented him from being selected for the England squad for the 2002 World Cup.

Woodgate was first called up to the England squad in April 1999, Kevin Keegan named him in the squad for the friendly against Hungary. However, he picked up an injury playing for Leeds United and had to withdraw from the squad. In May 1999, he was called up for the Euro 2000 qualifiers against Sweden and Bulgaria. On 9 June, Woodgate made his debut in the 1-1 draw against Bulgaria, he started the game before being replaced by Ray Parlour in the 64th minute. He retained his place in the squad for the Euro 2000 qualifiers against Luxembourg and Poland, but he didn't feature in either game. Woodgate was called up for the friendly against Belgium in October 1999, but he later withdrew from the squad because of a back injury. This turned out to be his last involvement with the England squad for nearly three years. The Football Association decided that Woodgate wouldn't be allowed to play for England until the court case stemming from an incident during a night out in Leeds in January 2000 was over, and any subsequent punishments served. This meant he would miss out on both Euro 2000 and the 2002 FIFA World Cup.

Woodgate began his career at Middlesbrough but moved to Leeds United at the age of sixteen after disagreements over his future between Middlesbrough and his family. He helped Leeds to win the FA Youth Cup in 1997, and in October the following year made his debut for the senior side. Woodgate was a consistent and impressive performer for Leeds during his time there, competing with the likes of Rio Ferdinand, Lucas Radebe and Dominic Matteo for a starting place. He was regarded as one of the most complete all round players to come through the Leeds academy, and performed for Leeds in a time when they competed in the UEFA Cup, Champions League and regularly finished towards the top of the Premier League.

Jonathan Simon Woodgate (born 22 January 1980) is a former footballer who played as a defender, and is the current manager of Middlesbrough.