Cleveland was born in Henryville, Indiana. He first learned to play violin at a local Suzuki program when he was 4 years old. His skill was recognized at an early age, with appearances on the Grand Ole Opry, A Prairie Home Companion and before the United States Congress in his early teens.
He currently lives in Charlestown, Indiana.
His first solo project on Rounder Records, Flame Keeper, won the International Bluegrass Music Association Instrumental Album of the Year in 2002, and he shared the same award with Tom Adams in 2004 for Tom Adams and Michael Cleveland Live at the Ragged Edge. His third award came for his 2006 album Let 'Er Go, Boys!.
Cleveland won the IBMA 2015 Fiddle Player of the Year and the 2010 Instrumental Group of the Year with his band Flamekeeper, for the third year. Cleveland had previously won Fiddle Player of the Year in 2001, 2002, 2004, 2006, 2007, 2008, 2009, 2010 and 2011.
In 2018 Cleveland was nominated for a Grammy Award for Best Bluegrass Album for his solo album, Fiddler's Dream.
In 2007, Cleveland and his band Flamekeeper entertained as part of the Bluegrass Sundays Winter Concert Series in Toronto, Ontario, Canada. The group performed at the Sally Creek Music Festival in Thames Centre, Ontario, in July, 2010.