Di Canio began his career in the Italian Serie A, playing for Lazio, Juventus, Napoli and Milan, before a brief spell with the Scottish club Celtic. He subsequently spent seven years in the English Premier League with Sheffield Wednesday, West Ham United and Charlton Athletic.
He was awarded the FIFA Fair Play Award after stopping a game when a goalkeeper was laying on the floor injured.
In January 1999, Di Canio signed for West Ham United for £1.5 million.
He scored the BBC Goal of the Season in March 2000 with a flying volley against Wimbledon, which is still considered among the best goals in Premiership history and was named as the Premiership's goal of the decade in a December 2009.
A talented yet controversial player, Di Canio was predominantly known for his creativity, eye for goal, technical ability, and dribbling skills, as well as his quick feet and intelligent play on the pitch.
During his playing career he made over 500 league appearances and scored over one hundred goals as a forward.