(*): W=Win, N=Nomination
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2005 | W | Video of the Year | "Whiskey Lullaby" | Brad Paisley |
| 2005 | W | Vocal Event of the Year | "Whiskey Lullaby" | Brad Paisley |
| 2005 | N | Top Vocal Group | - | Union Station |
| 2005 | N | Single Record of the Year | "Whiskey Lullaby" | Brad Paisley |
| 2004 | N | Vocal Event of the Year | "How's the World Treating You" | James Taylor |
| 1999 | N | Vocal Event of the Year | "Same Old Train" | Joe Diffie, Merle Haggard, Emmylou Harris |
| 1996 | N | Top New Female Vocalist | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2011 | N | Artist of the Year: Female | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2004 | N | Flame Worthy Collaborative Video of the Year | "How's the World Treating You" | James Taylor |
| 2002 | N | Flameworthy Hottest Video of the Year | "Let Me Touch You for Awhile" | Union Station |
| 2002 | N | Flameworthy Group / Duo Video of the Year | "The Lucky One" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2009 | N | Wide Open Country Video of the Year | "Please Read the Letter" | Robert Plant |
| 2009 | N | CMT Performance of the Year | "Gone Gone Gone (Done Moved On)" | Robert Plant |
| 2008 | W | Wide Open Country Video of the Year | "Gone, Gone, Gone (Done Moved On)" | Robert Plant |
| 2005 | W | Collaborative Video of the Year | "Whiskey Lullaby" | Brad Paisley |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2008 | W | Musical Event of the Year | "Gone, Gone, Gone" | Robert Plant |
| 2008 | N | Female Vocalist of the Year | - | - |
| 2007 | N | Musical Event of the Year | "Missing You" | John Waite |
| 2007 | N | Vocal Group of the Year | - | Union Station, Jerry Douglas |
| 2007 | N | Female Vocalist of the Year | - | - |
| 2006 | N | Vocal Group of the Year | - | Union Station, Jerry Douglas |
| 2005 | N | Female Vocalist of the Year | - | - |
| 2004 | W | Musical Event of the Year | "Whiskey Lullaby" | Brad Paisley |
| 2004 | W | Music Video of the Year | "Whiskey Lullaby" | - |
| 2004 | N | Female Vocalist of the Year | - | - |
| 2004 | N | Musical Event of the Year | "How's The World Treating You" | James Taylor |
| 2004 | N | Single of the Year | "Whiskey Lullaby" | - |
| 2003 | N | Female Vocalist of the Year | - | - |
| 2002 | N | Female Vocalist of the Year | - | - |
| 2002 | N | Vocal Event of the Year | "I'll Fly Away" | Gillian Welch |
| 2002 | N | Album of the Year | "New Favorite" | - |
| 2001 | W | Album of the Year | "O Brother, Where Art Thou?" (Soundtrack) | Gillian Welch, Emmylou Harris, John Hartford |
| 2001 | N | Vocal Event of the Year | "I'll Fly Away" | Gillian Welch |
| 2001 | N | Vocal Event of the Year | "Didn't Leave Nobody But The Baby" | Gillian Welch & Emmylou Harris |
| 1999 | N | Vocal Event of the Year | "Same Old Train" | Clint Black, Joe Diffie, Emmylou Harris |
| 1995 | W | Vocal Event of the Year | "Somewhere In The Vicinity of the Heart" | Shenandoah |
| 1995 | W | Single of the Year | "When You Say Nothing At All" | - |
| 1995 | W | Female Vocalist of the Year | - | - |
| 1995 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2006 | W | Bluegrass Recorded Song of the Year | "Living Prayer" | Union Station |
| 1998 | W | Bluegrass Recorded Song of the Year | "Children of the Living God" | Fernando Ortega |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2018 | N | Best American Roots Performance | "I Never Cared for You" | - |
| 2018 | N | Best Country Solo Performance | "Losing You" | - |
| 2012 | W | Best Bluegrass Album | "Paper Airplane" | Union Station |
| 2009 | W | Best Pop Collaboration with Vocals | "Rich Woman" | Robert Plant |
| 2009 | W | Best Country Collaboration with Vocals | "Killing the Blues" | Robert Plant |
| 2008 | W | Best Pop Collaboration with Vocals | "Gone Gone Gone (Done Moved On)" | Robert Plant |
| 2008 | N | Best Female Country Vocal Performance | "Simple Love" | - |
| 2006 | W | Best Country Performance by a Duo or Group with Vocal | "Restless" | Union Station |
| 2006 | W | Best Country Album | "Lonely Runs Both Ways" | Union Station |
| 2006 | W | Best Country Instrumental Performance | "Unionhouse Branch" | Union Station |
| 2005 | N | Best Country Collaboration with Vocals | "Coat Of Many Colors" | Shania Twain, Union Station |
| 2005 | N | Best Female Country Vocal Performance | "You Will Be My Ain True Love" | - |
| 2004 | W | Best Bluegrass Album | "Live" | Union Station |
| 2004 | W | Best Country Instrumental Performance | "Cluck Old Hen" | Union Station |
| 2004 | W | Best Country Collaboration with Vocals | "How's The World Treating You" | James Taylor |
| 2003 | N | Best Country Collaboration with Vocals | "Will the Circle Be Unbroken (Glory, Glory)" | Nitty Gritty Dirt Band,Taj Mahal, Doc Watson |
| 2002 | W | Best Country Performance by a Duo or Group with Vocal | "The Lucky One" | Union Station |
| 2002 | W | Best Bluegrass Album | "New Favorite" | Union Station |
| 2002 | W | Album of the Year | "O Brother Where Art Thou?" (Soundtrack) | Union Station, Emmylou Harris, Harley Allen, John Hartford, Mike Compton |
| 2002 | N | Best Country Instrumental Performance | "Choctaw Hayride" | Union Station |
| 2002 | N | Best Country Collaboration with Vocals | "Didn't Leave Nobody but the Baby" | Emmylou Harris, Gillian Welch |
| 2000 | N | Best Country Album | "Forget About It" | - |
| 2000 | N | Best Female Country Vocal Performance | "Forget About It" | - |
| 1999 | W | Best Country Collaboration with Vocals | "Same Old Train" | Clint Black, Dwight Yoakam, Earl Scruggs, Emmylou Harris |
| 1998 | W | Best Country Vocal Performance by a Duo or Group | "Looking In The Eyes Of Love" | Union Station |
| 1998 | W | Best Country Instrumental Performance | "Little Liza Jane" | Union Station |
| 1998 | W | Best Bluegrass Album | "So Long So Wrong" | Union Station |
| 1997 | W | Best Country Collaboration with Vocals | "High Lonesome Sound" | Vince Gill, Union Station |
| 1997 | N | Best Country Vocal Performance - Female | "Baby Mine" | - |
| 1996 | W | Best Country Collaboration with Vocals | "Somewhere in the Vicinity of the Heart" | Shenandoah |
| 1996 | W | Best Country Vocal Performance - Female | "Baby, Now That I've Found You" | - |
| 1995 | W | Best Southern, Country, or Bluegrass Gospel Album | "I Know Who Holds Tomorrow" | Cox Family |
| 1995 | N | Best Country Collaboration with Vocals | "Teach Your Children" | Kathy Mattea, Crosby, Stills & Nash |
| 1995 | N | Best Country Vocal Performance by a Duo or Group | "When You Say Nothing at All" | Union Station |
| 1993 | W | Best Bluegrass Album | "Every Time You Say Goodbye" | Union Station |
| 1991 | W | Best Bluegrass Recording | "I've Got That Old Feeling" | - |
| 1990 | N | Best Bluegrass Recording | "Two Highways" | Union Station |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2008 | N | Inspirational Bluegrass Artist | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2008 | N | Female Vocalist of the Year | - | - |
| 2007 | N | Female Vocalist of the Year | - | - |
| 2007 | N | Instrumental Group of the Year | - | Union Station, Jerry Douglas |
| 2007 | N | Vocal Group of the Year | - | Union Station, Jerry Douglas |
| 2007 | N | Entertainer of the Year | - | Union Station, Jerry Douglas |
| 2005 | N | Entertainer of the Year | - | Union Station |
| 2005 | N | Album of the Year | "Lonely Runs Both Ways" | Union Station |
| 2005 | N | Instrumental Group of the Year | - | Union Station |
| 2005 | N | Vocal Group of the Year | - | - |
| 2005 | N | Female Vocalist of the Year | - | - |
| 2005 | N | Gospel Recorded Performance of the Year | "A Living Prayer" | Union Station |
| 2004 | W | Recorded Event of the Year | "Livin� Lovin� Losin: Songs of the Louvin Brothers" | Ronnie Dunn, Rebecca Lynn Howard, Glen Campbell |
| 2003 | W | Album of the Year | "Alison Krauss + Union Station Live" | Union Station |
| 2002 | W | Album of the Year | "Down From the Mountain" | Union Station, Gillian Welch, David Rawlings |
| 2001 | W | Album of the Year | "O Brother, Where Art Thou?" (soundtrack) | Norman Blake, Emmylou Harris, The Cox Family |
| 2001 | W | Gospel Recorded Performance of the Year | "I'll Fly Away" | Gillian Welch |
| 1995 | W | Female Vocalist of the Year | - | - |
| 1995 | W | Entertainer of the Year | - | Union Station |
| 1993 | W | Female Vocalist of the Year | - | - |
| 1993 | W | Album of the Year | "Every Time You Say Goodbye" | Union Station |
| 1991 | W | Entertainer of the Year | - | Union Station |
| 1991 | W | Female Vocalist of the Year | - | - |
| 1991 | W | Album of the Year | "I've Got That Old Feeling" | Union Station |
| 1990 | W | Female Vocalist of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2014 | N | Female Vocalist of the Year | - | - |
| 2012 | N | Entertainer of the Year | - | - |
| 2012 | N | Female Vocalist | - | - |
| 2012 | N | Album of the Year | "Paper Airplane" | Union Station |
| 2012 | N | Song of the Year | "Dust Bowl Children" | Union Station, Peter Rowan |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2005 | N | Favorite Country Group | - | Union Station |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2004 | W | Best Original Song Written for Film (from movie "Cold Mountain" (2003)) | "You Will Be My Ain True Love" | Sting |
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