Born in Croydon, London to parents of Nigerian and Sierra Leonean heritage, Cole began his football career with Chelsea where he was a trainee in 2001.  His first debut came a short time later when he stepped in as a substitute against Everton in April 2002.  Less than a month later he started his first match against Middlesbrough and scored his first senior, professional goal.

Promoted to the Chelsea first team for the 2002 - 2003 season, Cole began the first match in style by scoring a goal and setting another up.  In November 2002, he went to Wolverhampton Wanderers for an extended period of two months, but was recalled early to Chelsea in January 2003.

The remainder of his first full season was very successful for Cole, and saw him score the winning goal against Bolton Wanderers in April 2003, when they played them looking for a UEFA Champions League place.

In July 2006, Cole signed a contract with West Ham United for an unknown fee, and scored in his first outing for the team in August 2006 against Charlton Athletic. His form continued to improve with regular starts, and in the 2008 - 2009 season he scored in all competitions and picked up assists for the team.  He signed a new five year contract in November 2008, identifying himself as a regular member of the first team.

At an international level, Cole chose not to play for either Nigeria or Sierra Leone, opting for the England team instead, playing his first match in February 2009 in a friendly against Spain, which he went on in as a substitute.