|| I've Got That Old Feeling || Best Bluegrass Recording || |- | || Every Time You Say Goodbye || Best Bluegrass Album || |- |rowspan="3"| || "When You Say Nothing At All" || Best Country Performance by a Duo or Group with Vocal || |- | "Teach Your Children" || Best Country Vocal Collaboration || |- | I Know Who Holds Tomorrow || Best Southern Gospel, Country Gospel or Bluegrass Gospel Album || |- |rowspan="2"| || "Baby, Now That I've Found You" || Best Female Country Vocal Performance || |- | "Somewhere in the Vicinity of the Heart" || Best Country Collaboration with Vocals || |- |rowspan="2"| || "Baby Mine" || Best Female Country Vocal Performance || |- | "High Lonesome Sound" || Best Country Collaboration with Vocals || |- |rowspan="3"| || "Looking in the Eyes of Love" || Best Country Performance by a Duo or Group with Vocal || |- | "Little Liza Jane" || Best Country Instrumental Performance || |- | So Long So Wrong || Best Bluegrass Album || |- | || "Same Old Train" || Best Country Collaboration with Vocals || |- |rowspan="2"| || "Forget About It" || Best Female Country Vocal Performance || |- | Forget About It || Best Country Album || |- |rowspan="5"| || O Brother, Where Art Thou? || Album of the Year || |- | New Favorite || Best Bluegrass Album || |- | "The Lucky One" || Best Country Performance by a Duo or Group with Vocal || |- | "Choctaw Hayride" || Best Country Instrumental Performance || |- | "Didn't Leave Nobody But The Baby" || Best Country Collaboration with Vocals || |- |rowspan="2"| || "Can the Circle Be Unbroken (By and By)" || Best Country Collaboration with Vocals || |- | This Side || Best Contemporary Folk Album || |- |rowspan="3"| || "How's The World Treating You" (with James Taylor) || Best Country Collaboration with Vocals || |- | "Cluck Old Hen" || Best Country Instrumental Performance || |- | Live || Best Bluegrass Album || |- |rowspan="2"| || "You Will Be My Ain True Love" || Best Female Country Vocal Performance || |- | "Coat of Many Colors" (with Shania Twain) || Best Country Collaboration with Vocals || |- |rowspan="3"| || "Restless" || Best Country Performance by a Duo or Group with Vocal || |- | "Unionhouse Branch" || Best Country Instrumental Performance || |- |