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On 25 August 2007, just a day after his 16th birthday, Fleck was included for the first time in the Rangers first team squad for a competitive match against [[Kilmarnock F.C.|Kilmarnock]]. He made his competitive debut on 23 January 2008 in the [[Scottish Cup]] game against [[East Stirlingshire F.C.|East Stirlingshire]]<ref name="Rangers 6-0 East Stirlingshire">{{cite news |url=http://news.bbc.co.uk/sport1/hi/football/scot_cups/7203278.stm |title=Rangers 6–0 East Stirlingshire |website=BBC Sport |date=23 January 2008}}</ref> and made his league debut on 22 May in the final league game of the season against [[Aberdeen F.C.|Aberdeen]]. Two days later, Fleck became the youngest ever player to play in a senior British cup final,<ref>{{cite news |url=https://www.telegraph.co.uk/sport/football/teams/rangers/6999350/Rangers-blow-as-John-Fleck-and-Danny-Wilson-seek-way-out.html |title=Rangers blow as John Fleck and Danny Wilson seek way out |last=Grahame |first=Ewing |date=15 January 2010 |newspaper=The Daily Telegraph |location=London |access-date=21 August 2011}}</ref> by appearing as a substitute in the [[2008 Scottish Cup Final]] against [[Queen of the South F.C.|Queen of the South]].<ref name=2008ScottishCupFinal>{{cite news |url=http://news.bbc.co.uk/sport1/hi/football/scot_cups/7416622.stm |title=Queen of the South 2–3 Rangers: Report |first=Clive |last=Lindsay |website=BBC Sport |date=24 May 2008 |access-date=22 February 2020}}</ref> He gained his first start for Rangers against [[Falkirk F.C.|Falkirk]] on 17 January 2009, earning the man of the match award for his performance.<ref>{{cite news |url=https://www.telegraph.co.uk/sport/football/teams/rangers/4285704/John-Fleck-has-the-talent-to-be-a-Rangers-great-says-Steven-Davis.html |title=John Fleck has the talent to be a Rangers great, says Steven Davis |newspaper=The Daily Telegraph |location=London |date=18 January 2009 |access-date=21 August 2011}}</ref> Five days before this, ''[[The Times]]'' had placed Fleck seventh in their Top 50 Rising Stars of football list.<ref name="Footballs Top 50 Rising Stars">{{cite news |url=http://www.timesonline.co.uk/tol/sport/football/european_football/article5502827.ece?token=null&offset=84&page=8 |title=Footballs Top 50 Rising Stars |newspaper=The Times |date=12 January 2009 |location=London |first=Tom |last=Dart |access-date=6 May 2010}}</ref>
Fleck scored his first competitive goal in a 2–0 league victory over [[Dundee United F.C.|Dundee United]] at [[Ibrox Stadium|Ibrox]] on 31 January 2009.<ref>{{ Cite news | url=http://news.bbc.co.uk/sport1/hi/football/scot_prem/7858967.stm | title=Rangers 2–0 Dundee United | website= BBC Sport | date=31 January 2009}}</ref> The goal was a 78th-minute penalty, awarded after [[Mihael Kovačević]]'s challenge had brought Fleck to the ground. Fleck's talent, precocious performances, technique, vision and work-rate led him to be heralded by some in the media as "Scotland's [[Wayne Rooney]]".<ref name=Rooney>{{cite news |url=https://www.telegraph.co.uk/sport/football/teams/rangers/4425378/Rangers-teenager-John-Fleck-hailed-as-Scotlands-Wayne-Rooney.html |title=Rangers teenager John Fleck hailed as Scotland's Wayne Rooney |newspaper=The Daily Telegraph |location=London |author1=Roddy Forsyth |date=1 February 2009 |access-date=15 September 2016}}</ref><ref>[http://www.heraldscotland.com/our-wayne-rooney-just-remember-ally-dick-1.833664 Our Wayne Rooney? Just remember Ally Dick], ''The Herald'', 6 February 2009</ref>
It was reported in August 2009 that Fleck had been dropped from the Rangers first-team after a training ground "bust-up" with the assistant manager, [[Ally McCoist]].<ref>{{ Cite news | url=http://news.bbc.co.uk/sport1/hi/football/teams/r/rangers/8180391.stm | title=Rangers drop Fleck after bust-up| website=BBC Sport| date=2 August 2009}}</ref> On 26 March 2010, Fleck signed a new three-year contract.<ref>{{cite news |url=http://news.bbc.co.uk/sport1/hi/football/teams/r/rangers/8589788.stm |title=Fleck signs new three-year deal |website=BBC Sport |date=26 March 2010}}</ref> That summer, he had a strong pre-season but then suffered a hamstring injury early in the campaign which hampered his progress.<ref>[https://www.eveningtimes.co.uk/news/13222969.forgotten-boy-in-blue-john-fleck-set-to-be-man-for-all-seasons/ Forgotten boy in blue John Fleck set to be man for all seasons], Evening Times, 7 July 2011</ref>
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