Montgomery Gentry, has been nominated in music awards more than three dozen times, including a Grammy nomination for "Lucky Man", but has only won twice.
Vocal Duo of the Year Top Vocal Duo Album of the Year  Back When I Knew It All Top Vocal Duo Vocal Duo of the Year Best Country Vocal Performance by a Duo or Group  "Lucky Man" Vocal Duo of the Year Top Vocal Duo Vocal Duo of the Year Top Vocal Duo Vocal Duo of the Year Top Vocal Duo Vocal Duo of the Year Top Vocal Duo Vocal Event of the Year  "The Truth About Men"
(with Tracy Byrd, Andy Griggs, and Blake Shelton) Vocal Duo of the Year Top Vocal Duo Vocal Duo of the Year Top Vocal Duo Vocal Duo of the Year Top Vocal Duo Vocal Duo of the Year Top New Vocal Duo or Group Top Vocal Duo Favorite New Artist  Country Vocal Duo of the Year 
Won Won Vocal Duo of the Year Top New Vocal Duo or Group Favorite New Artist  Country Won 
