In 1995 he began refereeing in the Football League, and since 1999 in the FA Premier League. In 2001 he was appointed as an official FIFA referee.
Bennett refereed the 2005 League Cup final at the Millennium Stadium between Chelsea and Liverpool, which the London club won by 3 goals to 2. In October 2005, he was in charge of the World Cup qualifier between Norway and Moldova, when the home side won 1-0 with a goal from Sigurd Rushfeldt.
He took charge of the UEFA Champions League quarter final first leg match in March 2006 between Benfica and Barcelona, the game ending 0-0. Barcelona won the return match 2-0, setting up a final with Arsenal.
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