(*): W=Win, N=Nomination
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2003 | N | Top Vocal Group | - | - |
| 2003 | N | Entertainer of the Year | - | - |
| 2003 | N | Album of the Year | "Home" | - |
| 2002 | N | Top Vocal Group | - | - |
| 2001 | W | Entertainer of the Year | - | - |
| 2001 | W | Top Vocal Group | - | - |
| 2001 | W | Video of the Year | "Goodbye Earl" | - |
| 2000 | W | Top Vocal Group | - | - |
| 2000 | W | Album of the Year | "Fly" | - |
| 2000 | N | Entertainer of the Year | - | - |
| 2000 | N | Single of the Year | "Ready to Run" | - |
| 2000 | N | Video of the Year | "Ready to Run" | - |
| 1999 | W | Top New Group | - | - |
| 1999 | W | Top Vocal Group | - | - |
| 1999 | N | Album of the Year | "Wide Open Spaces" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2003 | W | Favorite Country Band/Duo/Group (in January) | - | - |
| 2003 | W | Favorite Country Album (in January) | "Home" | - |
| 2003 | N | Favorite Country Band/Duo/Group (in November) | - | - |
| 2001 | W | Favorite Country Band/Duo/Group | - | - |
| 2000 | N | Favorite Country Band/Duo/Group | - | - |
| 2000 | N | Favorite Country Album | "Fly" | - |
| 1999 | W | Favorite New Country Artist | - | - |
| 1999 | N | Favorite Country Band/Group/Duo | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2017 | N | Top Country Tour | - | - |
| 2000 | W | Country Artist of the Year | - | - |
| 2000 | W | Country Album of the Year | "Fly" | - |
| 2000 | W | Country Duo/Group of the Year | - | - |
| 2000 | W | Country Albums Artist of the Year | - | - |
| 1999 | W | Country Artist of the Year | - | - |
| 1999 | W | Country Albums Artist of the Year | - | - |
| 1999 | W | Country Albums Artist Duo/Group of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2001 | W | Favorite Duo or Group - Country | - | - |
| 2000 | W | Favorite Duo or Group - Country | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2007 | N | Best Song (from movie "Shut Up and Sing" (2006)) | "The Neighbor" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2003 | N | Top Selling Album | "Home" | - |
| 2000 | W | Best Selling Album | "Fly" | - |
| 1999 | W | Best Selling Album | "Wide Open Spaces" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2002 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2020 | N | Video of the Year | "Gaslighter" | - |
| 2020 | N | Group Video of the Year | "Gaslighter" | - |
| 2007 | N | Video of the Year | "Not Ready to Make Nice" | - |
| 2007 | N | Group Video of the Year | "Not Ready to Make Nice" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2007 | N | Vocal Group of the Year | - | - |
| 2003 | N | Vocal Group of the Year | - | - |
| 2003 | N | Album of the Year | "Home" | - |
| 2002 | W | Vocal Group of the Year | - | - |
| 2001 | N | Entertainer of the Year | - | - |
| 2001 | N | Vocal Group of the Year | - | - |
| 2000 | W | Music Video of the Year | "Goodbye Earl" | - |
| 2000 | W | Album of the Year | "Fly" | - |
| 2000 | W | Vocal Group of the Year | - | - |
| 2000 | W | Entertainer of the Year | - | - |
| 2000 | N | Vocal Event of the Year | "Roly Poly" | - |
| 1999 | W | Vocal Group of the Year | - | - |
| 1999 | W | Music Video of the Year | "Wide Open Spaces" | - |
| 1999 | W | Single of the Year | "Wide Open Spaces" | - |
| 1999 | N | Entertainer of the Year | - | - |
| 1998 | W | - | - | - |
| 1998 | W | Vocal Group of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2000 | W | Group/Duo of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2020 | N | Most Empowering Classic Girl Power Anthem (Group or Duo) | "Goodbye Earl" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2007 | W | Best Country Album | "Taking the Long Way" | - |
| 2007 | W | Best Country Vocal Performance by a Duo or Group | "Not Ready to Make Nice" | - |
| 2007 | W | Song of the Year | "Not Ready to Make Nice" | Dan Wilson |
| 2007 | W | Album of the Year | "Taking the Long Way" | - |
| 2007 | W | Record of the Year | "Not Ready to Make Nice" | - |
| 2006 | N | Best Country Performance by a Duo or Group with Vocal | "I Hope" | - |
| 2005 | W | Best Country Vocal Performance by a Duo or Group | "Top of the World" | - |
| 2003 | W | Best Country Performance by a Duo/Group | "Long Time Gone" | - |
| 2003 | W | Best Country Instrumental Performance | "Lil' Jack Slade" | - |
| 2003 | W | Best Country Album | "Home" | - |
| 2003 | W | Best Recording Package | "Home" | Kevin Regan (art director) |
| 2003 | N | Album of the Year | "Home" | - |
| 2001 | N | Best Country Collaboration with Vocals | "Strong Enough" | Sheryl Crow |
| 2001 | N | Best Country Collaboration with Vocals | "Walk Softly" | Ricky Skaggs |
| 2000 | W | Best Country Album | "Fly" | - |
| 2000 | W | Best Country Performance by a Duo/Group | "Ready to Run" | - |
| 2000 | N | Album of the Year | "Fly" | - |
| 2000 | N | Best Country Collaboration with Vocals | "Roly Poly" | - |
| 1999 | W | Best Country Album | "Wide Open Spaces" | - |
| 1999 | W | Best Country Performance by a Duo or Group with Vocal | "There's Your Trouble" | - |
| 1999 | N | Best New Artist | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2007 | W | International Album of the Year | "Taking the Long Way" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2001 | N | Favorite Band | - | - |
| 2000 | N | Favorite Band | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2003 | W | Favorite Group | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2000 | W | Song of the Year: Country Radio | "Cowboy Take Me Away" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2004 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2007 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2001 | W | Group/Duo of the Year | - | - |
| 2001 | N | Entertainer of the Year | - | - |
| 2001 | N | - | - | - |
| 2001 | N | Music Video of the Year | "Goodbye Earl" | Evan Bernard |
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