Born in Hammersmith, London,[1] to an English mother and an Italian father,[2][3] Dichio began his career at Queens Park Rangers, joining as an apprentice in June 1991 and turning professional in May 1993.

[4] The sale of Les Ferdinand to Newcastle United in the summer of 1995 provided Dichio with the opportunity to break into QPR's first team in the 1995–96 Premier League season.

He scored on his league debut for QPR against Aston Villa, and forged a strike partnership with Kevin Gallen throughout the remainder of the season.

[6] Despite settling in the area, however, he failed to regain a starting place in the team and in October 2003, he joined Derby on loan,[7] scoring once against Ipswich Town.

Dichio, despite a difficult start to his Preston career, won over the fans at Deepdale causing many to be greatly upset as the news broke that his move to Toronto was to be finalised.

In April 2007, Dichio was released from his contract to let him join the newly created MLS club Toronto FC.

On 18 March 2009, he announced his intention to retire after the 2009 Major League Soccer season and to continue living in Toronto while also pursuing coaching opportunities.

[15] However, on 9 September 2009, Dichio officially announced his retirement with six games remaining on Toronto FC's season schedule.

[16] He remains much beloved of Toronto fans, who sing a song in his honour in the 24th minute of each game, commemorating his inaugural goal for the franchise (scored at 23:13 on 12 May 2007 vs. Chicago Fire).