Cole began his career at Chelsea in 2001, spending spells out on loan at Wolverhampton Wanderers, Charlton Athletic and Aston Villa before being transferred to West Ham United in 2006.

[9] He suffered a hairline fracture in his leg in August but returned to action in a League Cup tie against Gillingham on 6 November, scoring both Chelsea goals in a 2–1 home win in the third round.

[18] After the club's purchase by billionaire Roman Abramovich led to the signings of international strikers Adrian Mutu and Hernán Crespo, Cole went to Charlton Athletic on a season-long loan in August.

Despite Charlton being keen to retain Cole's services for the 2004–05 season,[20] he joined Aston Villa on a season-long loan in July 2004.

[8] He joined West Ham United in July 2006,[28] having made a total of 31 league and cup appearances for Chelsea, scoring eight goals.

[28] He scored seconds into his competitive debut for West Ham after coming on as a substitute in injury time to seal a 3–1 home win against Charlton on 19 August.

[30] On 26 October 2008, Cole received his first red card of his West Ham career against Arsenal, with a foul on Alex Song at Upton Park.

[citation needed] He scored ten Premier League goals, including one penalty in the 5–3 home win over Burnley on 28 November.

[49] On 19 May 2012, Cole scored the first goal, his 15th of the season, in West Ham's 2–1 win over Blackpool in the play-off final, ensuring an immediate return to the Premier League.

[51] Cole's first goal of the 2012–13 season came in a 3–1 victory against London rivals Chelsea on 1 December 2012, with a header inside the six-yard box to the near post.

[56] On 3 September 2013, after West Ham failed with a number of bids for strikers at the end of the transfer window, they approached Cole about returning to the club.

[65] His only other goals of the season came in a 3–1 away win at Burnley on 10 October and in a 2–2 home FA Cup draw against Everton on 13 January 2015, equalising in the 113th minute to make the match 2–2.

[69] Following his release, after nine years with West Ham, Cole stated his intention to seek at least three more seasons playing at the top-level of football.

[71] On 10 January 2016, he scored his only goal for Celtic in a 3–0 win over Stranraer at Stair Park, in the fourth round of the Scottish Cup.

[78] Cole was handed a trial by AFC Wimbledon in the beginning of January 2018 and immediately played for their development squad, where he scored a goal in his first game.

[79] According to the club's manager, Neal Ardley "Carlton's agent spoke to Simon Bassey [first-team coach] and asked about him coming in.

[85] In December 2018, Cole rejoined West Ham United to work with the club's academy players, providing support to under-18 coaches Jack Collison and Mark Phillips.

[86] In April 2011, Cole was fined £20,000 by The Football Association for comments he made on Twitter regarding England's friendly against Ghana, at Wembley Stadium the previous month, joking that the match was being used as a sting operation by immigration authorities.

[87] Cole was again charged by The Football Association in March 2015, when in response to a Tottenham fan taunting him on Twitter by asking whether he would consider retirement, he replied "Fuck off you cunt".

[89] On 28 November 2021, Cole and BBC Radio 5 Live apologised when he compared a possible overwhelming attack by Manchester City Football Club as a holocaust for their opponents.

[90] Cole accepted the offer to play in Indonesia as it was close to Malaysia, and his wife, Sofea, had returned there to live, in Kuala Lumpur.

[citation needed] Since retiring, Cole has been a pundit for talkSPORT, currently co-hosting Friday evening show The Sports Bar Weekender.