The Grammy Awards started handing out awards for the Category Best Classical Crossover Album in 1999. The Turtle Island String Quartet has won the award twice since its inception, once in 2006 and again in 2008.

Winners: Grammys Best Classical Crossover Album

Year
Winner/s
Album
2009
The King's Singers
Simple Gifts
2008
Turtle Island String Quartet
A Love Supreme: The Legacy of John Coltrane
2007
Bryn Terfel, London Voices & London Symphony Orchestra
Simple Gifts
2006
Turtle Island String Quartet & Ying Quartet
4 + Four
2005
Los Angeles Guitar Quartet
LAGQ's Guitar Heroes
2004
Jorge Calandrelli (conductor) & Yo-Yo Ma
Obrigado Brazil performed by various artists
2003
Sid McLauchlan (producer), Richard Lancaster, Ulrich Vette (engineers), André Previn (conductor) & the London Symphony Orchestra
Previn Conducts Korngold (Sea Hawk; Captain Blood, etc.)
2002
Edgar Meyer (producer), Robert Battaglia (engineer), Béla Fleck (producer & artist), Joshua Bell, Evelyn Glennie, Gary Hoffman, Edgar Meyer, Chris Thile & John Christopher Williams
Perpetual Motion
2001
Steven Epstein (producer), Richard King (engineer), Yo-Yo Ma, Edgar Meyer & Mark O'Connor
Appalachian Journey
2000
The Chestnut Brass Company & Peter Schickele - Schickele: Hornsmoke (Piano Concerto No. 2 in F Major "Ole"; Brass Calendar; Hornsmoke
A Horse Opera