Di Matteo scored the winner against Middlesbrough on his home debut for Chelsea. His passing ability and accurate long-distance shooting saw him become one of the driving forces of Chelsea's resurgence in the late 1990s. He contributed nine goals in his first season, including long-range efforts against both Tottenham Hotspur and Wimbledon. He helped the club finish sixth place in the league, their highest placing since 1989–90, and reach the 1997 FA Cup Final at Wembley. Within 42 seconds of the kick-off of the final against Middlesbrough, Di Matteo scored the opening goal from 30 yards and Chelsea won 2–0. Di Matteo's goal was the fastest in a Wembley FA Cup final until the record was broken by Louis Saha for Everton in 2009.