| Year | Association | Category | Nominated work | Result [1] [2] [3] |
|---|
| 1986 | Academy of Country Music | Top New Male Vocalist | — | Won |
| Album of the Year | Guitars, Cadillacs, Etc., Etc. | Nominated |
| Country Music Association | Horizon Award | — | Nominated |
| Music Video of the Year | "Honky Tonk Man" | Nominated |
| 1987 | Academy of Country Music | Country Music Video of the Year | "Little Sister" | Nominated |
| Grammy Awards | Best Country Song | "Guitars, Cadillacs" | Nominated |
| Best Male Country Vocal Performance | Guitars, Cadillacs, Etc. Etc. | Nominated |
| 1988 | Academy of Country Music | Top Vocal Duet | "Streets of Bakersfield" (with Buck Owens) | Nominated |
| Top Male Vocalist | — | Nominated |
| Album of the Year | Buenas Noches from a Lonely Room | Nominated |
| Country Music Association | Vocal Event of the Year | "Streets of Bakersfield" (with Buck Owens) | Nominated |
| Grammy Awards | Best Male Country Vocal Performance | Hillbilly Deluxe | Nominated |
| 1989 | Best Country Collaboration with Vocals | "Streets of Bakersfield" (with Buck Owens) | Nominated |
| Best Male Country Vocal Performance | Buenas Noches from a Lonely Room | Nominated |
| 1990 | Best Country Vocal Collaboration | "Sin City" (with k. d. lang) | Nominated |
| 1991 | Best Male Country Vocal Performance | "Turn It On, Turn It Up, Turn Me Loose" | Nominated |
| 1992 | Academy of Country Music | Top Vocal Duet | "Send a Message to My Heart" (with Patty Loveless) | Nominated |
| Country Music Association | Vocal Event of the Year | "Sweet Suzanne" (as part of Buzzin' Cousins) | Nominated |
| 1993 | Academy of Country Music | Album of the Year | This Time | Nominated |
| Single of the Year | "Ain't That Lonely Yet" | Nominated |
| Country Music Association | Nominated |
| 1994 | Male Vocalist of the Year | — | Nominated |
| Grammy Awards | Best Male Country Vocal Performance | "Ain't That Lonely Yet" | Won |
| Best Country Vocal Collaboration | "Miner's Prayer" (with Ralph Stanley) | Nominated |
| 1995 | Best Male Country Vocal Performance | "Pocket of a Clown" | Nominated |
| 1996 | "A Thousand Miles from Nowhere" | Nominated |
| Best Country Album | Dwight Live | Nominated |
| 1997 | Best Male Country Vocal Performance | "Nothing" | Nominated |
| Best Country Album | Gone | Nominated |
| 1998 | Academy of Country Music | Vocal Event of the Year | "Same Old Train" (with various artists) | Nominated |
| 1998 | Grammy Awards | Best Country Album | Under the Covers | Nominated |
| 1999 | Country Music Association | Vocal Event of the Year | "Same Old Train" (with various artists) | Nominated |
| Grammy Awards | Best Country Collaboration with Vocals | Won |
| 2000 | Best Male Country Vocal Performance | "Crazy Little Thing Called Love" | Nominated |
| 2001 | Country Music Association | Vocal Event of the Year | "Alright, I'm Wrong" (with Buck Owens) | Nominated |
| Grammy Awards | Best Male Country Vocal Performance | "A Thousand Miles from Nowhere" (re-recording) | Nominated |
| 2011 | Academy of Country Music | Cliffie Stone Pioneer Award | — | Won |
