Kenny Chesney Awards

2007
Academy of Country Music Award for Entertainer of the Year

2005
Academy of Country Music Award for Entertainer of the Year

2004
CMA Album of the Year
CMA Entertainer of the Year
CMT Flameworthy Video Music Award for Hottest Video of the Year
CMT Flameworthy Video Music Award for Male Video of the Year

2003
Academy of Country Music Award for Single of the Year
Academy of Country Music Award for Top Male Vocalist

2002
CMT Flameworthy Video Music Award for Male Video of the Year
CMT Flameworthy Video Music Award for Video of the Year

1997
Academy of Country Music Award for Top New Male Vocalist