He progressed quickly with Manchester United, and could have become the youngest player ever to appear in their first team when he was selected in their squad for the final fixture of the 1999–2000 FA Premier League season, against Aston Villa on 14 May 2000. This plan was stymied as Premier League rules prohibited players on schoolboy contracts from appearing at the senior level, and his debut was delayed. He had been part of the reserve team that won the Manchester Senior Cup in 1999–2000. Fletcher was initially seen as a right midfielder, similar to David Beckham, and was tipped by many to break into the first-team with ease and stay there for many years to come. As he developed he came to be viewed more as a central midfielder.