| Year | Awards | Award |
|---|---|---|
| 1994 | Country Music Television | Male Video Artist of the Year |
| American Music Awards | Album of the Year – Not a Moment Too Soon | |
| American Music Awards | Top New Male Vocalist | |
| Billboard Awards | Top New Country Artist | |
| Billboard Magazine | Top New Country Album – Not a Moment Too Soon | |
| 1995 | American Music Awards | Favorite Country New Artist |
| 1997 | Billboard Magazine | Single of the Year – "It's Your Love" (with Faith Hill) |
| Country Music Television | Video of the Year – "It's Your Love" (with Faith Hill) | |
| Country Music Television | Male Artist of the Year | |
| Playgirl Magazine | Top Ten, Sexiest Men of the Year | |
| CMA | Vocal Event – "It's Your Love" (with Faith Hill) | |
| 1998 | Billboard Awards | Country Single of the Year – "Just To See You Smile" |
| CMA | Album of the Year – Everywhere | |
| Academy of Country Music | Single of the Year – "It's Your Love" (with Faith Hill) | |
| Academy of Country Music | Song of the Year – "It's Your Love" (with Faith Hill) | |
| Academy of Country Music | Video of the Year – "It's Your Love" (with Faith Hill) | |
| Academy of Country Music | Top Vocal Event – "It's Your Love" (with Faith Hill) | |
| 1999 | Academy of Country Music | Male Vocalist |
| Academy of Country Music | Vocal Collaboration – "Just to Hear You Say That You Love Me" (with Faith Hill) | |
| CMA | Male Vocalist | |
| CMA | Album of the Year – A Place in the Sun | |
| 2000 | CMA | Male Vocalist |
| National Fatherhood Initiative | Father of the Year | |
| Academy of Country Music | Male Vocalist | |
| Billboard Awards | Male Artist of the Year | |
| 2001 | American Music Awards | Favorite Male Country Artist |
| Grammy Awards | Vocal Collaboration – "Let's Make Love (with Faith Hill) | |
| CMA | Entertainer of the Year | |
| Billboard Awards | Country Artist | |
| Billboard Awards | Male Country Artist | |
| Billboard Awards | Country Albums Artist | |
| Billboard Awards | Country Single Artist | |
| Billboard Awards | Country Album – Greatest Hits | |
| 2002 | American Music Awards | Best Country Album – Set This Circus Down |
| American Music Awards | Favorite Male Country Artist | |
| 2003 | American Music Awards (January) | Favorite Country Male Artist |
| Radio Music Awards (January) | Country Male Artist | |
| American Music Awards (November) | Favorite Country Male Artist | |
| 2004 | People's Choice Awards | Favorite Country Male Artist |
| Radio Music Awards | Country Male Artist | |
| CMA | Single of the Year – "Live Like You Were Dying" | |
| 2005 | American Music Awards | Album of the Year -Live Like You Were Dying |
| American Music Awards | Male Artist (country genre) | |
| Academy of Country Music | Song of the Year -"Live Like You Were Dying" | |
| Academy of Country Music | Single of the Year -"Live Like You Were Dying" | |
| People's Choice Awards | Favorite Country Male Artist | |
| Grammy Award | Best Male Country Vocal Performance – "Live Like You Were Dying" | |
| Country Music Television | Most Inspiring Video – "Live Like You Were Dying" | |
| 2006 | People's Choice Awards | Top Male Performer |
| Grammy Award | Country Vocal Collaboration – "Like We Never Loved At All" (with Faith Hill) | |
| 2012 | CMA | Musical Event of the Year - "Feel Like a Rock Star" (with Kenny Chesney) |
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