• 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 been awarded as Best Country Vocal Collaboration

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

Table of contents

1 2000s 2 1990s 3 1980s

2000s

• 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 "I am a 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"

• 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"