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On 21 January 2019, Cole joined Championship side Derby County, reuniting with manager Frank Lampard who was his teammate at Chelsea and with England. He signed a contract until the end of the 2018–19 season. He was released at the end of the season. On 18 August 2019, Cole officially announced his retirement.

Head coach Sigi Schmid named Cole as captain ahead of the 2018 season. The Galaxy missed the play-offs again. He was released by LA Galaxy at the end of their 2018 season.

In his second season in California, Cole saw another red card on 23 August 2017 after 18 minutes of a 2–0 loss at Columbus Crew SC for a foul on Pedro Santos. He played 29 matches for the Galaxy, scoring once in a 6–2 home loss to Real Salt Lake, as the team came dead last and missed out on the play-offs for the first time since 2008.

Cole signed with LA Galaxy of Major League Soccer on 27 January 2016. On 24 February, he made his debut in a goalless home draw against Santos Laguna in the CONCACAF Champions League; on 6 March, he made his league debut in the first game of the 2016 season, playing the full 90 minutes of a 4–1 win over D.C. United at the StubHub Center. Manager Bruce Arena praised Cole and fellow veteran new signing Nigel de Jong after the result. On 1 May, he was sent off for a second booking in a 1–1 draw at Sporting Kansas City. Cole was ejected following a clumsy tackle on Benny Feilhaber after being cautioned just 32 seconds earlier. He received his second dismissal of the season on 25 June in the match against San Jose Earthquakes. Cole had been booked for a reckless tackle and as emotions were high, a melee ensued. The referee deemed Cole's reaction worthy of another booking and as a result he received his marching orders for the second time in eight league games.

On 7 August 2016, Cole scored his first goal for the Galaxy, a last-minute equaliser in a 2–2 home draw against the New York Red Bulls. His team qualified for the 2016 MLS Cup Playoffs, where they lost the Western Conference semi-finals to the Colorado Rapids on penalties. Cole's attempt was saved by Colorado goalkeeper Tim Howard, and after the game he apologised publicly to his long-time England teammate Steven Gerrard, who was playing his final professional match for the Galaxy that night.

During the 2013–14 season, Cole was dropped from the Chelsea team, with César Azpilicueta replacing him as the club's first choice left-back in the month of November. Cole captained the team on the last match day against Cardiff City in a 2–1 away win which turned out to be his last in a Chelsea shirt. On 23 May 2014, after the end of the season, he was included on the list of players released by Chelsea. Cole's contract expired on 30 June 2014.

On 7 July 2014, Cole signed a two-year deal with Roma. He made his competitive debut on 30 August in their first game of the Serie A season, playing the full 90 minutes of a 2–0 win over Fiorentina at the Stadio Olimpico. On 19 January 2016, Cole terminated his contract with Roma with one year of his contract remaining.

On 11 May 2014, he announced his retirement from international football after being omitted from the England squad for the 2014 FIFA World Cup.

Cole was given the number 3 shirt at Chelsea, and made his first appearance for the club as a substitute for Wayne Bridge in their 2–1 win over Charlton Athletic on 9 September. He issued a public statement concerning his transfer saying he "forgave" Arsenal for how he felt he was treated during his time there.

On 22 January 2013, Cole signed a one-year extension to his contract with Chelsea. Cole again helped the club win a European title during the 2012–13 season, playing in a 2–1 victory over Benfica in the 2013 UEFA Europa League Final on 15 May.

Liam Brady described Cole as a player with "great character and determination" and his former teammate Sylvinho noted that one of Cole's qualities was being competent: "Ashley does not need people saying, 'Do this' or 'Go there'. He knows, he knows." The rapid progress made by Cole in his debut season for Arsenal "surprised" Wenger and prompted him to make the defender his first pick. Sylvinho, the player displaced, commented that Wenger's belief in Cole helped him to develop as a player: "He spoke to [Cole] and said: 'After Silvinho you can play left-back. You are one of the best left-backs at the club and one day will be one of the best in the world.'" Cole's link-up play with winger Robert Pires and main striker Thierry Henry in a 4–4–2 formation effectively made him "a wing-back or winger playing in a back four" because Arsenal's game emphasised attacking football.

In the 2011–12 season, Cole won the seventh FA Cup of his career after Chelsea beat Liverpool 2–1 in the 2012 FA Cup Final. In the Champions League semi-finals against Barcelona, Cole was pivotal in Chelsea's 1–0 victory which included a goal-line clearance that denied Barça an away goal. Cole also received praise for his role in the final against Bayern Munich on 19 May 2012, both for his defending, and for scoring in the decisive penalty shoot-out as Chelsea won the club's first European Cup.

Cole scored his first goal for over two years against Stoke City on 22 September 2012, proving to be the winner. On 1 December 2012, Cole made his 350th Premier League appearance, in a 3–1 away loss to West Ham United.

On 27 February 2011, Cole accidentally shot Tom Cowan, a 21-year-old sports science student on work experience at Chelsea, with a .22 calibre air rifle from only five feet away at the club's Cobham Training Centre, apparently unaware that the rifle was loaded. Cole formally apologised to Cowan, and discussed the incident with Chelsea officials.

He made his 79th appearance for England on 12 June 2010 in the 1–1 draw against the United States in the 2010 World Cup Group stage match. He beat the record of 79 caps by a black English international (John Barnes, who appeared for England from 1983 to 1995) when he played against Algeria later that month. He has played more internationals without scoring than any other outfield player in England history. He won his 86th cap against Montenegro in October 2010, and alongside Kenny Sansom, Cole is now England's most-capped full-back in history, an achievement which helped him pick up the England Player of the Year award for 2010, as voted for by fans. On 6 February 2013, he earned his 100th cap as England beat Brazil 2–1 at Wembley.

Arsenal had offered Cole a longer contract to stay at the club, but he had been left "trembling with anger" when they offered him wages of £55,000 per week. His wage increased to £120,000 a week when he signed a new contract in September 2009.

After starting Chelsea's first six games in the league, Cole scored his third, fourth and fifth Chelsea goals at home to Burnley, Tottenham Hotspur and Sunderland respectively. On 2 September 2009, he signed a new four-year deal which will contract him to Chelsea until 2013. On 10 February 2010, he suffered a fractured left ankle in the 2–1 defeat against Everton that kept him out of action for three months. He eventually made his return against Stoke City, a game which Chelsea won 7–0. Cole scored a goal against Wigan Athletic on the last day of the Premier League in an 8–0 win as Chelsea claimed the title. He then played in the 2010 FA Cup Final, where Chelsea beat Portsmouth to give Cole the second league and cup double of his career. He started all 38 league games for Chelsea in the 2010–11 season, and was awarded the Chelsea F.C. Player's Player of the Year award for the second time.

Cole has had a couple of minor brushes with the police. On 4 March 2009 he was held after swearing in front of a police officer outside a South Kensington nightclub. He was taken to a police station and issued with an £80 Fixed Penalty Notice before being released. On 4 January 2010, Cole was convicted of a speeding offence committed on 17 November 2009. He was recorded exceeding the speed limit by doing 104 mph in a 50 mph zone on the A3 road in Kingston upon Thames, a residential stretch. His defence at Kingston Magistrates Court, opposing the charge in his absence, argued unsuccessfully that the police speed gun was faulty. Cole also claimed that his actions were excuseable because he was trying to evade the paparazzi. On 29 January he was fined £1000 and disqualified from driving for four months.

Cole was reportedly one of the players upset when José Mourinho was relieved of his position as Chelsea manager. He was dropped in favour of Wayne Bridge for the 2008 Football League Cup Final, which Chelsea lost 2–1 to Tottenham Hotspur. However, Cole scored his first Chelsea goal in Chelsea's very next game, on 1 March 2008, the fourth goal in a 4–0 away victory against West Ham United. On 19 March 2008, Cole was involved in a controversial incident in a Premier League game against Tottenham at White Hart Lane where he performed a high tackle on Tottenham's Alan Hutton. Referee Mike Riley gave Cole a yellow card, a decision which was judged as too lenient by some analysts. Cole allegedly also "turned his back on the referee" and the episode renewed debate in the media over the game's rules on dissent towards officials.

On 31 January 2007, Cole suffered a serious knee injury in the 3–0 victory over Blackburn Rovers in a Premier League game at Stamford Bridge, although after a scan it was revealed to be not as bad as first thought, with Chelsea optimistic that he would return before the end of the 2006–07 season. Cole did indeed make a return at the end of the season, playing in the last twelve minutes of the 2007 FA Cup Final at the new Wembley Stadium against Manchester United. Chelsea emerged victorious 1–0 after extra-time with a goal scored by Didier Drogba, to win the 2007 FA Cup.

In August 2006, after a protracted transfer saga, Cole completed a move to rival club Chelsea, with whom he won further honours, including the Premier League in the 2009–10 season, four FA Cups, one Football League Cup and one UEFA Champions League. He was released by Chelsea at the end of the 2013–14 season. With seven winners' medals, Cole has won the FA Cup more times than any other player in history, and is one of two players to have won the Double with two clubs, along with Nicolas Anelka.

On 28 July 2006, Arsenal vice-chairman David Dein confirmed that Arsenal and Chelsea had been in "civil talks" about the player. Chelsea insisted they would not raise their £16million bid for Cole, but Arsenal held out for at a higher valuation of £25 million. Negotiations continued throughout August and looked to be heading for deadlock, but eventually Cole signed for Chelsea on 31 August for a fee of £5 million, with William Gallas being transferred from Chelsea to Arsenal as part of the same deal. The deal was closed after the transfer window had officially ended, and was not confirmed until an hour and a half after the deadline had passed. The move angered Arsenal fans, who dubbed him "Cashley" and waved fake £20 notes with Cole's face on them at him when the two clubs faced each other on 10 December 2006.

Cole was also an ever-present for England in the 2006 World Cup; in their second round match against Ecuador he made a crucial block, deflecting Carlos Tenorio's shot onto the crossbar. The match ended with England winning 1–0, but the team were knocked out on penalties by Portugal in the quarter-finals. By the end of 2008, Cole had achieved 68 caps for England, all of which were starting appearances.

Cole began a relationship with Girls Aloud singer Cheryl Tweedy in September 2004, when they were living in the same block of flats in London; they married on 15 July 2006 in Wrotham Park, Hertfordshire. In January 2008, the couple almost separated after allegations were made that Cole had affairs with three other women. He, however, disputed the allegations and the couple stayed together. It was announced on 23 February 2010 that the couple would separate following new allegations of adultery. Three months later, it was announced that Cheryl was filing for divorce. They officially divorced on 3 September 2010. Cole has a son (born 2016) and a daughter (born 2018) with the Italian model Sharon Canu.

In 2006, Cole sued the News of the World and The Sun newspapers for libel after they printed allegations that he was involved in a "homosexual orgy". Both papers retracted the allegations. That same year, Cole released an autobiography titled, My Defence, which sold 4,000 copies in the first six weeks of release. Cole's former teammate, Jens Lehmann, criticised Cole for writing an autobiography when he was 25.

Cole was found guilty of making contact with league rivals Chelsea over a possible move, without informing Arsenal. He was fined £100,000 by the Premier League on 2 June 2005 for a tapping-up meeting at a hotel in January 2005. Cole, his agent Jonathan Barnett, the Chelsea manager José Mourinho and chief executive Peter Kenyon were present at the meeting. An appeal in August 2005 did not reject the guilty verdict, but his fine was reduced to £75,000. Chelsea were also fined £300,000 and Mourinho was fined £200,000, reduced on appeal in August 2005 to £75,000. Barnett's licence was suspended for 18 months and he was also fined £100,000.

On 18 July 2005, Cole signed a one-year extension to his contract with Arsenal, but just a year later departed from the club in acrimonious circumstances. On 15 July 2006, Cole launched a verbal attack on Arsenal; in his autobiography, he claimed that the Arsenal board had treated him as a "scapegoat" and that they had "fed him to the sharks" over the tapping-up affair while Arsenal, from their part, insisted that they were legally obliged to punish Cole for his illegal contact with Chelsea. Cole was deliberately left out of Arsenal's 2006–07 team photograph, fuelling press speculation that he would leave.

Cole had a very good season in 2004–05. He was a regular at left-back for both England and Arsenal despite Gaël Clichy's claim for a place in the first team squad. Cole scored his first goal of the season in the seventh game in a tough trip to Manchester City in which he scored the opening and only goal to give Arsenal an important win. He scored his second goal in a 3–1 away win to Aston Villa, scoring Arsenal's third in only the 28th minute.

With Arsenal, he won the FA Premier League twice (in 2002 and 2004), and the FA Cup three times (in 2002, 2003 and 2005, scoring in the penalty shootout in the final of the latter). Although injured for much of the 2005–06 season, he recovered in time to play in Arsenal's UEFA Champions League Final defeat to Barcelona at the end of the season. In total he made 228 first-team appearances for the Gunners, scoring nine goals.

Cole is renowned for making timed goal-line clearances and "cutting out danger". In a league match against Tottenham Hotspur in December 2002, he made two notable clearances, which demonstrated to him that his defensive game had improved. He also made two goal line clearances in Chelsea's 2011–12 Champions League winning campaign. The first was against Napoli, in a 3–1 round-of-16 first leg defeat, and the second in Chelsea's semi-final first leg 1–0 win against Barcelona. Both were vital as Chelsea went on to win the ties with a margin of one goal on aggregate, eventually lifting the Champions League. Cole is said to have a "mean streak", and has been labelled a "dirty player", something which he himself and his former coaches have strongly denied.

Cole was an England international from 2001 to 2014, playing at the 2002, 2006 and 2010 World Cups, as well as Euro 2004 and Euro 2012. He was voted England Player of the Year in 2010. When he retired from international football in 2014, he had won 107 caps, making him England's most-capped full-back.

After just four appearances for the Under-21s, Cole was fast-tracked into the England senior team and Sven-Göran Eriksson handed Cole his senior international debut against Albania, on 28 March 2001. He played for England at the 2002, 2006 and 2010 FIFA World Cups, UEFA Euro 2004 (where he was named as one of four England players in the all-star squad for the tournament) and UEFA Euro 2012.

Cole started his career by joining his local club, Arsenal, whom he had supported as a child. At the age of 18, on 30 November 1999, he made his first team debut in the League Cup fourth round against Middlesbrough; Arsenal lost 1–3 on penalties after the match ended 2–2 at the end of extra time at the Riverside Stadium. On 25 February 2000, he signed his first professional contract. His Premier League debut came on 14 May 2000 against Newcastle United, as part of an experimental side that lost 4–2 away on the final day of the season. Before he fully broke into the Arsenal side, he spent part of the 1999–2000 season on loan at Crystal Palace, where he played 14 league matches and scored one goal, a long-range half-volley against Blackburn Rovers. When Sylvinho, Arsenal's established left-back, suffered an injury in the autumn of the 2000–01 season, Cole took the opportunity to establish himself in the first team and remained first-choice even after the Brazilian's recovery.

Cole has played for England at youth and senior levels. He was capped for the England U-20 team at the 1999 FIFA World Youth Championship alongside Stuart Taylor, Peter Crouch, Andrew Johnson and Matthew Etherington. However, the team finished bottom of their group, suffering three defeats without scoring any goals. He also made four appearances for England under-21s, scoring once.

Ashley Cole (born 20 December 1980) is an English former footballer who played as a left-back, most notably for Premier League club Chelsea, with whom he presently serves in the coaching staff for the U15 team. Cole is considered by many critics and fellow professional players as one of the best defenders of his generation, and by some, for the better part of his career, as the best left-back in the world. Born in Stepney, London, Cole began his youth career at Arsenal and made his full debut for the club in November 1999, going on to make 228 appearances and scoring nine goals for the North London club. With Arsenal he won two Premier League titles, three FA Cups, and was an integral member of the "Invincibles" team of the 2003–04 season, who went the entire league season undefeated. Cole also made an appearance in Arsenal's first UEFA Champions League final in 2006; the club lost 2–1 to Barcelona.