The Grammy Award for Best Country Collaboration with Vocals was an honor presented at the Grammy Awards, a ceremony that was established in 1958 and originally called the Gramophone Awards, to quality country music collaborations for artists who do not normally perform together.
Originally called the Best Country Vocal Performance, Duet, the award was first presented to Kenny Rogers and Ronnie Milsap at the 30th Grammy Awards in 1988 for the single "Make No Mistake, She's Mine". The next year, the category's name was changed to Best Country Vocal Collaboration, a name it held until 1996 when it was awarded as the Best Country Collaboration with Vocals. In 2011, the category was merged with the Grammy Award for Best Country Performance by a Duo or Group with Vocal and the Grammy Award for Best Country Instrumental Performance, forming the Grammy Award for Best Country Duo/Group Performance in order to "tighten the number of categories" at the Grammy Awards.
Alison Krauss holds the record for having the most wins in this category, with a total of five. She is followed by seven others, who have all won the award twice. Among the most nominated are Emmylou Harris and Willie Nelson, both nine-time nominees. Krauss was nominated eight times, while Dolly Parton was a seven-time hopeful. Nominated bands include 1996 winners Shenandoah, a five-man country music band, three-time nominees the Nitty Gritty Dirt Band, as well as one of the award's final recipients, the Zac Brown Band.
Recipients
thumb|right|upright|alt=A woman wearing a brown jacket and playing a fiddle.|Five-time award winner [[Alison Krauss]]
thumb|right|upright|[[41st Annual Grammy Awards|1999 and 2000 award winner Emmylou Harris|alt=A Caucasian woman with white hair playing a guitar]]
thumb|right|upright|[[45th Annual Grammy Awards|2003 and 2008 award winner Willie Nelson]]
thumb|right|upright|[[k.d. lang, one of two winners born outside of the United States|alt=A face shot of a Caucasian women with black hair and brown eyes]]
thumb|right|upright|[[51st Annual Grammy Awards|2009 award winner Carrie Underwood collaborated with Randy Travis]]
{| class="wikitable sortable plainrowheaders"
! scope="col" style="width:5em;" | Year
! scope="col" | Performing artists
! scope="col" | Work
! scope="col" class="unsortable" | Nominees
! scope="col" class="unsortable" | Ref.
|-
! scope="row" |1988
| with Kenny Rogers
|
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| align="center"|
|-
! scope="row"|1989
| and k.d. lang
|
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| align="center"|
|-
! scope="row" |1990
| with Hank Williams, Sr.
|
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| align="center"|
|-
! scope="row" |1991
| and Mark Knopfler
|
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| align="center"|
|-
! scope="row" |1992
| with Vince Gill, Ricky Skaggs and Steve Wariner
|
|
| align="center"|
|-
! scope="row" |1993
| featuring Marty Stuart
|
|
| align="center"|
|-
! scope="row" |1994
| with Linda Davis
|
|
| align="center"|
|-
! scope="row" |1995
| and Trisha Yearwood
|
|
| align="center"|
|-
! scope="row" |1996
|
