Switzerland and Italy
Born in Switzerland to Italian parents from the Abruzzo region, Di Matteo began his career with Swiss club Schaffhausen, before joining Aarau in 1991. He was playing with such football stars as Daniel Rubli. He won the Swiss Nationalliga A with Aarau in 1993 and in the same season achieved Switzerland's Player of the Year award. He signed for Lazio in the summer of 1993 on a free transfer. Di Matteo became a regular in the Lazio side and made his debut for Italy during his three seasons with the Rome club. However, a falling out with coach Zdeněk Zeman over a defensive error which resulted in a loss to Internazionale, ended his career with the Lazio. As a result he was signed by Ruud Gullit for English side Chelsea for a then club record fee of £4.9 million.Chelsea
Di Matteo made an impressive start to his Chelsea career, scoring the winner against Middlesbrough on his home debut.[2] 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, Di Matteo scored from 30 yards, to set Chelsea on their way to a 2–0 win versus Middlesbrough. This was the quickest goal scored in a cup final at the old Wembley, although Louis Saha has since broken the record for the fastest goal scored in an FA Cup final - scoring in 25 seconds against Chelsea for Everton in the 2009 final.The following season he 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. The 1998–99 season turned out to be a special season for Chelsea as they went on an unbeaten run of over 20 games to finish third in the Premier League and qualify for the Champions League. Di Matteo played a pivotal role in midfield next to Gustavo Poyet, Dennis Wise and Dan Petrescu and scored some memorable goals, among them a strike against Coventry City in the dying seconds of the game.
During the 1999–2000, season he was hampered 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 spent the next eighteen months on the sidelines. He eventually gave up on his comeback and retired in February 2002 at the age of 31.[3] In his six years at Chelsea, he made 175 appearances and scored 26 goals. He never lost at Old Trafford.[4] He was selected in the squad of Chelsea's greatest ever XI, and former manager Claudio Ranieri handed him 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.
Management career
Milton Keynes Dons
In July 2008, Di Matteo was appointed as Milton Keynes Dons new manager after Paul Ince left to join Blackburn Rovers.[5] He in turn appointed former Chelsea colleague Eddie Newton as his assistant and Ade Mafe, who appeared at the 1984 Summer Olympics and worked at Chelsea during Di Matteo's time there, as his fitness coach. He began qualifying for his UEFA coaching licences while still playing – completing his "B" licence during his time with Chelsea. In his first season with MK Dons, he led them to third place in League One behind Leicester City and Peterborough. They lost in the play-offs semi-finals against Scunthorpe on penalties.West Bromwich Albion
He was hired as West Bromwich Albion Head Coach. In his first season, the team finished second in the English second division, the Football League Championship, behind favourites Newcastle United, winning automatic promotion to the Premier League.On the opening day of the 2010–11 Premier League season (14 August 2010) Roberto Di Matteo paid a return visit to Stamford Bridge as head coach of West Brom, but saw his side lose 0-6 to Chelsea. Better results in following matches led to the best start in a Premier League Season by the club, and Di Matteo was also named Premier League Manager of the Month for September 2010.[6] During December 2010 and January 2011, the club had a period of poor form, winning only one of ten matches. The majority of fans were still loyal to Di Matteo but after a 0-3 defeat to Manchester City on 5 February 2011 he was relieved of his duties with immediate effect.[7] and first-team coach Michael Appleton was appointed caretaker manager.[8] West Bromwich finished the season in eleventh position.
Chelsea
After a failed application to become Birmingham City manager[9], Di Matteo was announced as the assistant manager to new Chelsea manager Andre Villas-Boas on the 29 June 2011,.[9][10] On 4 March 2012 he was appointed caretaker manager of Chelsea until the end of the season following the sacking of Villas-Boas.[11] Di Matteo started his reign at Chelsea in winning form, after a 2-0 victory over Birmingham City in the FA Cup and going through to the Quarter Finals of the FA cup. On 10 March 2012, Di Matteo got his first league win against Stoke City, winning 1-0 thanks to second half Didier Drogba goal. On 14 March, in the 2nd leg of a Champions League Last 16, Chelsea overcame a 3-1 deficit against SSC Napoli to win 4-1 on the night, on aggregate 5-4 to qualify for the Champions League Quarter Finals, becoming only the fourth team in 45 attempts to overturn a first leg deficit of two goals or more.[12] He also guided the Blues to a 5-2 victory over Leicester City, with Fernando Torres getting a brace to put Chelsea through to the Semi Final of the FA Cup. His first loss as Chelsea manager came when Manchester City defeated them 2-1 at the Etihad Stadium. In the Quarter final of the Champions League, Chelsea defeated SL Benfica 3-1 on aggregate, after winning 1-0 away, as well beating them at Stamford Bridge, setting up a Semi-final with reigning Champions FC Barcelona. His side defeated Aston Villa at Villa Park, in between the two Quarter final legs, on 31 March, with a final score of 4-2 with form-finding striker Fernando Torres scoring one of the four goals. His team then won against Wigan Athletic with a score of 2-1 and drew with Fulham 1-1. They then thrashed Tottenham Hotspur 5-1 in the Semi Final taking the Blues into the final where they will meet Liverpool on 5 May.[13] In the Champions League Semi-final first leg match, his side defeated FC Barcelona 1-0 thanks to a Didier Drogba goal - a surprise to many observers, as the Catalan side had recently come into some form, with a string of victories leading up to the tie.[14]On 24th April 2012, Di Matteo led Chelsea to a 3-2 aggregate win over FC Barcelona in the UEFA Champions League semi-final by achieving a 2-2 draw in the second leg game at the Nou Camp home stadium of the Spanish club - thus taking the west London team to their first UEFA Champions League final since May of 2008, when they lost to Manchester United on penalties.[15].
On 29 April, Di Matteo gave Chelsea their first league derby win of the season, as they defeated Queens Park Rangers at Stamford Bridge by a scoreline of 6-1, with Torres' hattrick being accompanied by goals by Daniel Sturridge, John Terry and Florent Malouda.
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