Born in Leicester, England but of Antiguan descent, Heskey grew up in the area where his father, Tyrone, operated security for the local nightclubs.  His early football career began with Ratby and Groby Juniors, and his talent led him to join Leicester City’s Football Academy when he was 9 years old.  He went on to sign a professional contract with them, and on 8 March 1995, at the age of 17, he played his debut match for them against Queens Park Rangers

The 1995 - 1996 season saw him become a regular player in the first team, at the end of which Leicester City were promoted to the Premier League.  He stayed with the team until near the end of the 1999 - 2000 season, helping them with the League Cup twice in that time.

In March 2000 Heskey moved to Liverpool in an £11 million deal, making his debut in a Premier League match against Sunderland on 11 March 2000.  He scored his first goal for his new team in a 3 - 0 win over Coventry City less than a month later.  The 2000 - 2001 season saw Heskey produce 23 goals, and there was talk of a £12 million move to Tottenham Hotspur as a result.  The deal never came to fruition and Heskey remained with Liverpool for another two years.

Heskey signed a contract with Wigan Athletic on 7 July 2006 for £5.5 million, making his debut a month later in a defeat to Newcastle United.

In January 2009, when his contract with Wigan had expired, Heskey signed a contract with Aston Villa for £3.5 million.  He played his debut against Portsmouth in the same month, scoring with a 20 yard strike, but scored only one more goal for Villa in the rest of the season.

At international level, Heskey played for the junior teams before getting called up to the seniors on 18 November 1998 for a friendly against the Czech Republic, although he never got to play.  He debuted against Hungary in April 1999 and played for the England team many times over the years.  His last goal for the international side came in a 2010 World Cup qualifier against Kazakhstan which England won 4 -0.