In recognition of his sterling work for the reserves, on 24 July 2008, Cleverley was called up to the Manchester United first team for the remainder of their tour of South Africa and the match against Portsmouth in Nigeria. He made his first team debut against Kaizer Chiefs in the final of the 2008 Vodacom Challenge, coming on in place of Rodrigo Possebon at half-time, before he scored the third of United's four goals just after the hour mark.
He returned to regular reserve team duty for the 2008–09 season, but was given a first team squad number 35 when the first team squad list was announced on 15 August 2008, and was named on the bench for United's League Cup matches against Middlesbrough and Queens Park Rangers.
On 18 August 2009, Cleverley signed for Watford on loan. He was then able to play in the Hornets' match away to Nottingham Forest that evening. He started the match and was booked within four minutes of the start of the second half, but then sealed a 4–2 win with a goal in the second minute of injury time at the end of the game. Cleverley returned to Manchester United for the 2010–11 season, and travelled with the squad for their pre-season tour of the United States in July 2010.
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