He joined Slough Town playing in 24 games and scoring on six occasions. He then moved to Bromley in January 2007. In total McCleary made over 40 appearances for Bromley scoring 11 goals. Nottingham Forest manager Colin Calderwood offered him a trial at the City Ground where he did well enough to secure a contract on 31 January 2008.

McCleary made his first team debut as an 87th-minute substitute, in a 1–0 home defeat against Carlisle United, on 3 March 2008. He scored his first goal for the club on 1 April 2008 in injury time, in a 2–0 win at Carlisle. On 5 April he was handed his first start where he was voted Man of the Match as Forest beat Cheltenham Town 3–1 at the City Ground.

In the 2011/12 season McCleary scored nine goals after returning from injury in December 2011; six of which came in March 2012. Four came in a high-scoring game away to Leeds United at Elland Road, where Forest won 7–3. These performances resulted in McCleary being named as the Football League Championship Player of the Month. He was voted Forest’s Player of the Season by the Forest supporters, beating Joel Lynch and Chris Gunter into second and third respectively.

On 16 May 2012 it was announced that McCleary had turned down a new contract at Forest and instead signed a three-year contract at Reading and fulfill his dream of playing in the Premier League. His first goal for Reading came in a 3–3 draw with Fulham.

In October 2012 he was earmarked by the Jamaica Football Federation to play for Jamaica during their 2014 World Cup qualifying campaign. He received his first call up on 24 January 2013 alongside Reading teammates Jobi McAnuff and Adrian Mariappa for the World Cup qualifier against Mexico on 6 February. McCleary started the match and helped Jamaica to a 0–0 draw at the Estadio Azteca.

McCleary signed a new contract with Reading on 3 October 2014, keeping at the club until the summer of 2017, before again extending it on 17 January 2017, this time until the summer of 2020.

On 4 November 2020 it was announced by Wycombe manager during a live webcast that the club had signed McCleary, who had been training with the club as a free transfer until the end of the current season.