 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.He made his competitive debut on 23 January 2008 in the Scottish Cup game against East Stirlingshire and made his league debut on 22 May in the final league game of the season against Aberdeen.Two days later, Fleck became the youngest ever player to play in a senior British cup final, by appearing as a substitute in the 2008 Scottish Cup Final against Queen of the South.