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