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 6th 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 an FA Cup final until the record was
broken by Louis Saha for Everton in 2009.The following season Di Matteo again proved his worth to the team, chipping in with ten goals and numerous assists, as Chelsea went on to claim the Football League Cup and the Cup Winners' Cup, their first European honour since 1971. In the League Cup final, again against Middlesbrough, Di Matteo scored the second goal in a 2–0 win. Di Matteo played in midfield next to Gustavo Poyet, Dennis Wise and Dan Petrescu in the 1998-99 season as Chelsea finished third.
During the 1999–2000 season Di Matteo was sidelined by injury but returned late in the season to score a handful of crucial goals, including his third Cup-winning goal at Wembley, once again in the FA Cup. In a dour match, Di Matteo capitalised on an error by Aston Villa goalkeeper David James to score the winner in the 71st minute, handing Chelsea their fourth major trophy in three years. This lead Di Matteo to comment on the old Wembley Stadium saying "It's a shame they're tearing the old place down – it has been a very lucky ground for me".
Early into the 2000–01 season, Di Matteo sustained a triple leg fracture in a UEFA Cup tie against Swiss side St. Gallen and did not play for the next eighteen months. He gave up on hopes of returning from this injury in February 2002 and retired at the age of 31.In "gratitude for the midfielder's contribution to the transformation of the club", then-manager Claudio Ranieri handed Di Matteo the honour of leading the Chelsea team out in the 2002 FA Cup Final, which Chelsea went on to lose 2–0 to London rivals Arsenal.
Di Matteo was selected in a Chelsea greatest-ever XI.In his six years at Chelsea, he made 175 appearances and scored 26 goals. He never lost at Old Trafford.
After an unsuccessful application to become manager of Birmingham City , Di Matteo was appointed Assistant Manager to André Villas-Boas, the new manager of Chelsea FC, on the 29 June 2011.
On 4 March 2012, following the dismissal of Villas-Boas, Di Matteo became caretaker manager for the club until the end of the season.. Officially according to Chelsea he is "Interim first team coach" . He started his tenure at Chelsea in winning form, with victories over Birmingham City in a fifth round FA Cup match; Stoke City in the Premiership; and SSC Napoli in the last 16 round of the UEFA Champions League competition - winning the second leg 4-1 (achieving a 5-4 aggregate score) in one of the most thrilling games ever seen at Stamford Bridge.
Di Matteo's Chelsea won against Tottenham in the FA Cup semi-final and Benfica in the UEFA Champions League quarter-final. On 24 April 2012, Di Matteo led Chelsea to a 3-2 aggregate win over heavily-favoured Barcelona in the UEFA Champions League semi-final by achieving a 1-0 victory in the first leg at Stamford Bridge followed by a 2-2 draw in the second leg at the Nou Camp.
Di Matteo's Chelsea won 2-1 against Liverpool in the 2012 FA Cup Final held at Wembley Stadium.
Di Matteo's future as coach could hinge on whether Chelsea becomes European champion for the first time in the club's 107-year history but he has captain John Terry, defender Branislav Ivanovic and midfield pair Ramires and Raul Meireles suspended.
If defender David Luiz fails to recover from injury, Di Matteo acknowledged that he could struggle to find seven experienced substitutes to fill his bench against Bayern Munich.
"With the suspensions we have, I'm still trying to find some solutions," Di Matteo said.
With Roy Hodgson having left West Bromwich Albion to take over as England coach, there is a vacancy at the club Di Matteo led into the Premier League two years ago. The Italian, though, is not interested in going back.
Di Matteo praised the "passion and heart'' of his players, especially after Bayern went ahead in the 83rd minute through Thomas Mueller, before Didier Drogba equalized in the 88th.
