The Grammy Award for Best Country Collaboration with Vocals was first handed out in 1988 as Best Country Vocal Performance, Duet. The title of the award was changed in 1989 to Best Country Vocal Collaboration; in 1996 it was revised again to the current title Best Country Collaboration with Vocals. The criteria for the award require artists who do not normally perform with each other.

Winners: Best Country Collaboration with Vocals

Year
Winner/s
Song
2010
Carrie Underwood & Randy Travis
"I Told You So"
2009
Robert Plant & Alison Krauss
"Killing the Blues"
2008
Willie Nelson & Ray Price
"Lost Highway"
2007
Bon Jovi & Jennifer Nettles
"Who Says You Can't Go Home"
2006
Faith Hill & Tim McGraw
"Like We Never Loved at All"
2005
Loretta Lynn & Jack White
"Portland, Oregon"
2004
James Taylor & Alison Krauss
"How's the World Treating You"
2003
Willie Nelson & Lee Ann Womack
"Mendocino County Line"
2002
Harley Allen, Pat Enright & Dan Tyminski (The Soggy Bottom Boys)
"Man of Constant Sorrow"
2001
Faith Hill & Tim McGraw
"Let's Make Love"
2000
Emmylou Harris, Dolly Parton & Linda Ronstadt
"After the Gold Rush"
1999
Clint Black, Joe Diffie, Merle Haggard, Emmylou Harris, Alison Krauss, Patty Loveless, Earl Scruggs, Ricky Skaggs, Marty Stuart, Pam Tillis, Randy Travis, Travis Tritt & Dwight Yoakam
"Same Old Train"
1998
Garth Brooks & Trisha Yearwood
"In Another's Eyes"
1997
Alison Krauss & Union Station & Vince Gill
"High Lonesome Sound"
1996
Alison Krauss & Shenandoah
"Somewhere in the Vicinity of the Heart"
1995
Aaron Neville & Trisha Yearwood
"I Fall to Pieces"
1994
Linda Davis & Reba McEntire
"Does He Love You"
1993
Marty Stuart & Travis Tritt
"The Whiskey Ain't Workin' "
1992
Vince Gill, Ricky Skaggs & Steve Wariner
"Restless"
1991
Chet Atkins & Mark Knopfler
"Poor Boy Blues"
1990
Hank Williams, Jr. & Hank Williams, Sr.
"There's a Tear in My Beer"
1989
k.d. lang & Roy Orbison
"Crying"
1988
Ronnie Milsap & Kenny Rogers
"Make No Mistake, She's Mine"
1987
Dolly Parton, Linda Ronstadt & Emmylou Harris
Trio