He retired from international cricket on 26 March 2008. Fleming played in the 2008 Indian Premier League for the Chennai Super Kings after being signed for US$350,000 and became the team's coach from 2009. In February 2015 he was signed as coach of the Melbourne Stars of the Big Bash League. On 19 January 2018 he resumed his duties as head coach of the Chennai Super Kings in 2018 Indian Premier League season again, after the team was barred from playing in the tournament for two seasons. He coached the Rising Pune Supergiant during this time.