1999 Grammy Award:
Best Country Album - FLY
1999 Grammy Award: Best Country Vocal Performance by a Duo or Group - "Ready to Run"
1999 Billboard Award:
Country Artist of the Year
1999 Billboard Award:
Country Artist Duo/Group of the Year
1999 Billboard Award:
Country Album Artist of the Year
1999 Billboard Award: Best New Country Artist Clip of the Year - "Ready to Run"
1999 CMA Award: Single of the Year "Wide Open Spaces"
1999 CMA Award: Music Video of the Year "Wide Open Spaces"
1999 CMA Award: Vocal Group of the Year
1999 WB Radio Music Awards: Country Song of the Year - "Wide Open Spaces"
1999 WB Radio Music Awards: Country Artist of the Year
1999 Grammy Award: Best Country Album
1999 Grammy Award: Best Country Vocal Performance/Duo or Group: "There's Your Trouble"
1999 ACM: Album of the Year: Wide Open Spaces
1999 ACM: Top Newl Duo/Group
1999 AMA: Favorite New Artist (Country)
1999 British Country Music Award: International Rising Star
1999 Canadian Country Music Award: Best Selling Album - Wide Open Spaces
