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Roberto Di Matteo
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===Chelsea=== Di Matteo scored the winner against [[Middlesbrough F.C.|Middlesbrough]] on his home debut for [[Chelsea F.C.|Chelsea]].<ref>{{cite news|title=Di Matteo breaks Chelsea deadlock|first=Glenn|last=Moore|url=https://www.independent.co.uk/sport/di-matteo-breaks-chelsea-deadlock-1310957.html|work=The Independent|publisher=Independent Print|location=London|date=21 August 1996|access-date=15 March 2012}}</ref> His passing ability and accurate long-distance shooting saw him become one of the driving forces of Chelsea's resurgence in the late 1990s, along with several other Italian players.<ref name="Italian Job">{{cite web |url=https://bleacherreport.com/articles/2668163-how-chelseas-italian-job-helped-make-the-club-great-again |title=How Chelsea's Italian Job Helped Make the Club Great Again |publisher=Bleacher Report |last1=Hayes |first1=Garry |date=12 October 2016 |access-date=2 May 2022 }}</ref> He contributed nine goals in his first season, including long-range efforts against both [[Tottenham Hotspur F.C.|Tottenham Hotspur]] and [[Wimbledon F.C.|Wimbledon]].{{citation needed|date=December 2015}} He helped the club finish sixth place in the league, their highest placing since [[1989β90 in English football|1989β90]], and reach the [[1997 FA Cup final]] at [[Wembley Stadium (1923)|Wembley]].{{citation needed|date=December 2015}} Within 42 seconds of the kick-off of the final against Middlesbrough, Di Matteo scored the opening goal from 30 yards and Chelsea won 2β0.<ref>{{cite web |title=Chelsea joy as Boro finish on empty |url=http://www.fa-carling.com/news/prem/17059719.html |website=fa-carling.com |publisher=Bass Brewery |date=17 May 1997 |access-date=25 October 2014 |archive-url=https://web.archive.org/web/19970613210614/http://www.fa-carling.com/news/prem/17059719.html |archive-date=13 June 1997}}</ref> Di Matteo's goal was the fastest in a Wembley FA Cup final until the record was broken by [[Louis Saha]] for [[Everton F.C.|Everton]] in [[2009 FA Cup final|2009]].{{citation needed|date=December 2015}} The following season Di Matteo again proved his worth to the team, contributing ten goals and numerous assists, as Chelsea went on to claim the [[EFL Cup|Football League Cup]] and the [[UEFA Cup Winners' Cup|Cup Winners' Cup]], their first European honour since 1971.{{citation needed|date=December 2015}} In the [[1998 Football League Cup final|League Cup final]], again against Middlesbrough, Di Matteo scored the second goal in a 2β0 win.{{citation needed|date=December 2015}} Di Matteo played in midfield next to [[Gus Poyet]], [[Dennis Wise]] and [[Dan Petrescu]] in the [[1998β99 Chelsea F.C. season|1998β99 season]] as Chelsea finished third.{{citation needed|date=December 2015}} During the [[1999β2000 FA Premier League|1999β2000]] 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 [[2000 FA Cup final|FA Cup]].{{citation needed|date=December 2015}} In a dour match, Di Matteo capitalised on an error by [[Aston Villa F.C.|Aston Villa]] goalkeeper [[David James (footballer, born 1970)|David James]] to score the winner in the 72nd minute, handing Chelsea their fourth major trophy in three years.<ref>{{cite news|title=Chelsea claim FA Cup glory|url=http://news.bbc.co.uk/2/hi/sport/football/fa_cup/756784.stm|publisher=BBC Sport|date=20 May 2000 |access-date=31 October 2016}}</ref><ref>{{cite web|last=Twomey|first=Liam|title=Chelsea's history of Italian managers a mixed bag with Conte to arrive|url=http://www.espnfc.com/club/chelsea/363/blog/post/2814492/chelsea-history-of-italian-managers-a-mixed-bag|work=ESPN FC|publisher=ESPN Internet Ventures|date=4 April 2016|access-date=31 October 2016}}</ref> This led 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".<ref>{{cite book|last1=Borrows|first1=Bill|first2=Derek|last2=Hammond|title=The talkSPORT Book of Premier League Legends|location=London|publisher=[[Simon & Schuster]]|page=273|date=2 August 2012|isbn=978-1-84983-941-9}}</ref> Early into the [[2000β01 FA Premier League|2000β01]] season, Di Matteo sustained a triple leg fracture in a [[UEFA Europa League|UEFA Cup]] tie against Swiss side [[FC St. Gallen|St. Gallen]] and did not play for the next eighteen months.<ref name="Injury_BBC">{{cite news|title=Roberto di Matteo named as new Chelsea assistant coach|url=https://www.bbc.com/sport/football/13957547|publisher=BBC Sport|date=29 June 2011|access-date=27 January 2013}}</ref><ref name="Injury_UEFA">{{cite web|title=Roberto Di Matteo|url=https://www.uefa.com/uefachampionsleague/news/0250-0c50fb933519-68896ee24d6a-1000--roberto-di-matteo/|publisher=UEFA|date=7 October 2014|access-date=30 October 2016}}</ref> He gave up on hopes of returning from this injury in February 2002 and retired at the age of 31.<ref name="Injury_BBC"/><ref name="Injury_UEFA"/> In his six years at Chelsea, Di Matteo made 175 appearances and scored 26 goals.<ref name="Roberto_LMA">{{cite web|title=ROBERTO DI MATTEO|url=http://www.leaguemanagers.com/managers/roberto-di-matteo/|website=leaguemanagers.com|publisher=[[League Managers Association]]|access-date=1 October 2015}}</ref>
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