[25] 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.

[28] 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.

[35] 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.

[36] 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.

[37] 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.

[39] 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.

[43] 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.

[45] In the Champions League semi-final against Barcelona, Cole was pivotal in Chelsea's 1–0 victory which included a goal-line clearance that denied Barça an away goal.

[46] 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 their first European title.

[51] 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.

[52] 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.

[55][56] 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.

Manager Bruce Arena praised Cole and fellow veteran new signing Nigel de Jong after the result.

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.

[63] 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.

[64] 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.

[65] 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.

[66] He played 29 matches for the Galaxy, scoring once in a 6–2 home loss to Real Salt Lake,[67] as the team came dead last and missed out on the play-offs for the first time since 2008.

[71] On 21 January 2019, Cole joined Championship side Derby County, reuniting with manager Frank Lampard who was his teammate at Chelsea and with England.

[80] When Wayne Rooney was appointed manager of EFL Championship club Birmingham City in October 2023, Cole joined his staff as a first-team coach.

[82] On 23 August 2024, it was confirmed that Cole would assist Carsley in his role as interim head coach of the England senior team following the departure of Gareth Southgate.

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.

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.

He beat the record of 79 caps by a black English international (John Barnes, who appeared for England from 1983 to 1995)[86] when he played against Algeria later that month.

"[92] The rapid progress made by Cole in his debut season for Arsenal "surprised" Wenger and prompted him to make the defender his first pick.

[95] Under José Mourinho at Chelsea, Cole's attacking threat was restrained, meaning it allowed the player to focus more on defending and marking.

[102][103] 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.

[108] 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".

His defence at Kingston Magistrates' Court, opposing the charge in his absence, argued unsuccessfully that the police speed gun was faulty.