*Grammy's Best Country Performance by a Duo or Group With Vocal (NRTMN), Song Of The Year (NRTMN), Best Country Album (TTLW), Record Of The Year (NRTMN), Album Of The Year (TTLW)
*Grammy's Best Country Performance By A Duo Or Group With Vocal (TOTW)
*American Music Award's Country Group/Duo Of The Year, Country Album Of The Year
*Grammy's Best Country Performance(LTG), Best Country Instrumental Performance(Lil' Jack Slade), Best Country Album(Home), Best Recording Package(Home)
*People's Choice for [tied with Creed] Favorite Musical Group or Band
*Top Grossing Act with over $49 million (without touring)
*French Association of Country Music's Video of the Year for "I Believe in Love"
*Defenders of Democracy Award
*Country Group/Duo Of The Year, Country Album Of The Year
*International Artist Achievement Award
*VH1's Big in 2003 Awards Big Quote of '03
*First Country act to advance their release date. First women too.
*CMA's Vocal Group of the Year
*Flameworthy's Music Video Visionary Award
*American Music Awards - Best Country Group or Duo.
*ACM's Entertainer, Vocal Group, Video of the Year
*Blockbuster Awards' Favorite Country Duo or Group
*Grammy Awards - Country Performance [Ready To Run], Country Album [Fly].
*ACM - Vocal Duo/Group, Album Of The Year [Fly].
*Blockbuster Entertainment Awards - Country Favorite Duo or Group.
*CW/TNN Awards - Vocal Duo/Group, Album [Fly].
*CMA - Video Of The Year [Goodbye Earl], Vocal Group Of The Year, Album Of The Year [Fly], Entertainer Of The Year.
*Radio & Records' Group of the Year
*Radio Music Awards - Country Song Of The Year [Cowboy Take Me Away].
*Billboard Music Awards - Country Artist, Country Album [Fly], Country Group Of The Year.
*Pollstar's #1 Country Touring Act w/ over $40 million
*CMT's Group Of The Year.
*Entertainment Weekly's - Best Of The Breed.
*HMV British Country Music Awards' Group/Duo and Album, "Fly."
*CCMA's Top Selling Album (FLY) - 2000
*Cosmopolitan Magazine's Best Band
*American Music Awards - Favorite New Country Artist.
*Grammy Awards - Country Performance [There's Your Trouble], Country Album [Wide Open Spaces].
*ACM - New Vocal Duo/Group, Top Vocal Duo/Group, Album Of The Year.
*Country Weekly Golden Pick - Favorite New Group/Duo.
*TNN/MCN Awards - Vocal Band Of The Year, Female Star Of Tomorrow.
*CMA - Video Of The Year [Wide Open Spaces], Single Of The Year[Wide Open Spaces], Vocal Group Of The Year.
*WB Awards: Song of the Year Country, Artist of the Year Country tied w/ Shania Twain
*Billboard Music Awards - Country Video Clip Of The Year, Country Artist Of The Year, *Country Group/Duo, Country Album [Wide Open Spaces].
*CMT - Top Video [Ready To Run].
*WomenOfCountry.com's Album of the Year, Video of the Year(RTR), Best Group or Duo
*Billboard's Country Artist of the Year, Country Group/Duo, Country Album
*CMT's "Video Group/Duo Of The Year", #1 and #7 Video
*Amazon.com: WOS #11, FLY #20 - Top 100 C.d's of 1999
*Joan River's "Worst Dress" @ Grammy's
*Gavin 1999's Breakthrough Artist
*CMA - Vocal Group Of The Year, Horizon.
*CMT - Rising Star.
*Roughstock - Best New Artist.
*Billboard's Top New Country Artist
*Entertainment Weekly's Breakout Acts