Answer: 42 seconds
Di Matteo joined Chelsea from Lazio in 1996. In the 1997 FA Cup Final he scored after only 42 seconds against Middlesbrough. It was, at the time, the fastest goal to be scored in an FA Cup final at Wembley. Chelsea went on to win the match 2-0. Di Matteo also won the FA Cup in 2000 with Chelsea, as well as the 1998 UEFA Cup Winners' Cup and the 1998 UEFA Super Cup. He suffered a leg break in 2001, which eventually forced him to retire from playing eighteen months later at the age of only 31.
Di Matteo would go on to manage Chelsea, winning the FA Cup and UEFA Champions League, both in 2012. This was the first time in their history Chelsea had won the Champions League. Despite this, poor form the following season saw Di Matteo fired in November 2012.