The Grammy Award for Best Country Collaboration with Vocals was first awarded in 1988. The award has had several minor name changes:

• In 1988 the award was known as Best Country Vocal Performance, Duet
• From 1989 to 1995 it was awarded as Best Country Vocal Collaboration
• From 1996 to the present it has been awarded as Best Country Collaboration with Vocals

The current eligibility criteria require that the artists do not normally perform together.

Years reflect the year in which the Grammy Awards were presented, for works released in the previous year.

2000s

• Grammy Awards of 2008
  • Willie Nelson & Ray Price for "Lost Highway"
• Grammy Awards of 2007
  • Bon Jovi & Jennifer Nettles for "Who Says You Can't Go Home"
• Grammy Awards of 2006
  • Faith Hill & Tim McGraw for "Like We Never Loved at All"
• Grammy Awards of 2005
  • Loretta Lynn & Jack White for "Portland, Oregon"
• Grammy Awards of 2004
  • James Taylor & Alison Krauss for "How's the World Treating You"
• Grammy Awards of 2003
  • Willie Nelson & Lee Ann Womack for "Mendocino County Line"
• Grammy Awards of 2002
  • Harley Allen, Pat Enright & Dan Tyminski (The Soggy Bottom Boys) for "Man of Constant Sorrow"
• Grammy Awards of 2001
  • Faith Hill & Tim McGraw for "Let's Make Love"
• Grammy Awards of 2000
  • Emmylou Harris, Dolly Parton & Linda Ronstadt for "After the Gold Rush"

1990s

• Grammy Awards of 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 for "Same Old Train"
• Grammy Awards of 1998
  • Garth Brooks & Trisha Yearwood for "In Another's Eyes"
• Grammy Awards of 1997
  • Alison Krauss & Union Station & Vince Gill for "High Lonesome Sound"
• Grammy Awards of 1996
  • Alison Krauss & Shenandoah for "Somewhere in the Vicinity of the Heart"
• Grammy Awards of 1995
  • Aaron Neville & Trisha Yearwood for "I Fall to Pieces"
• Grammy Awards of 1994
  • Linda Davis & Reba McEntire for "Does He Love You"
• Grammy Awards of 1993
  • Marty Stuart & Travis Tritt for "The Whiskey Ain't Workin' "
• Grammy Awards of 1992
  • Vince Gill, Ricky Skaggs & Steve Wariner for "Restless"
• Grammy Awards of 1991
  • Chet Atkins & Mark Knopfler for "Poor Boy Blues"
• Grammy Awards of 1990
  • Hank Williams, Jr. & Hank Williams, Sr. for "There's a Tear in My Beer"

1980s

• Grammy Awards of 1989
  • k.d. lang & Roy Orbison for "Crying"
• Grammy Awards of 1988
  • Ronnie Milsap & Kenny Rogers for "Make No Mistake, She's Mine"
• Grammy Awards of 1987
  • Dolly Parton Linda Ronstadt & Emmylou Harris for Trio