 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, which he won.