(*): W=Win, N=Nomination
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1981 | N | Best Music, Original Song [from movie "Honeysuckle Rose" (1980)] | "On the Road Again" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2018 | N | Vocal Event of the Year | "Funny (How Time Slips Away)" | Glen Campbell |
| 2017 | W | - | - | - |
| 2003 | N | Vocal Event of the Year | "Beer for My Horses" | Toby Keith |
| 1986 | W | Single Record of the Year | "Highwayman" | Johnny Cash, Waylon Jennings, Kris Kristofferson |
| 1986 | N | Video of the Year | "Highwayman" | Johnny Cash, Waylon Jennings, Kris Kristofferson |
| 1986 | N | Album of the Year | "Highwayman" | Johnny Cash, Waylon Jennings, Kris Kristofferson |
| 1985 | W | Single Record of the Year | "To All the Girls I've Loved Before" | Julio Iglesias |
| 1985 | N | Top Vocal Duo | - | Julio Iglesias |
| 1985 | N | Entertainer of the Year | - | - |
| 1984 | N | Top Vocal Duo | - | Merle Haggard |
| 1984 | N | Single Record of the Year | "Poncho & Lefty" | Merle Haggard |
| 1984 | N | Entertainer of the Year | - | - |
| 1984 | N | Album of the Year | "Poncho & Lefty" | Merle Haggard |
| 1983 | W | Album of the Year | "Always on My Mind" | - |
| 1983 | W | Single Record of the Year | "Always on My Mind" | - |
| 1983 | N | Top Male Vocalist | - | - |
| 1983 | N | Top Vocal Duo | - | Waylon Jennings |
| 1983 | N | Entertainer of the Year | - | - |
| 1981 | N | Entertainer of the Year | - | - |
| 1980 | W | Entertainer of the Year | - | - |
| 1980 | N | Album of the Year | "Willie Sings Kristofferson" | - |
| 1979 | N | Album of the Year | "Stardust" | - |
| 1979 | N | Song of the Year | "Mama Don't Let Your Babies Grow Up to Be Cowboys" | Waylon Jennings |
| 1979 | N | Single Record of the Year | "Mama Don't Let Your Babies Grow Up to Be Cowboys" | Waylon Jennings |
| 1979 | N | Entertainer of the Year | - | - |
| 1979 | N | Single Record of the Year | "Georgia On My Mind" | - |
| 1977 | N | Top Vocal Group | - | Waylon Jennings |
| 1977 | N | Single Record of the Year | "Good Hearted Woman" | Waylon Jennings |
| 1977 | N | Album of the Year | "Wanted Outlaws" | Jessie Colter, Waylon Jennings, Tom Paul Glaser |
| 1976 | N | Album of the Year | "Red Headed Stranger" | - |
| 1976 | N | Single Record of the Year | "Blue Eyes Crying in the Rain" | - |
| 1976 | N | Song of the Year | "Blue Eyes Crying in the Rain" | - |
| 1976 | N | Top Male Vocalist | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1987 | W | Favorite Country Male Artist | - | - |
| 1986 | W | Favorite Country Male Artist | - | - |
| 1986 | W | Favorite Country Single | "Forgiving You Is Easy" | - |
| 1986 | N | Favorite Country Album | "City of New Orleans" | - |
| 1985 | W | Favorite Country Male Video Artist | - | - |
| 1985 | N | Favorite Country Video | "Tougher Than Leather" | - |
| 1984 | W | Favorite Country Male Artist | - | - |
| 1984 | N | Favorite Country Video | "Pancho & Lefty" | Merle Haggard |
| 1983 | W | Favorite Country Album | "Always On My Mind" | - |
| 1982 | W | Favorite Country Single | "On the Road Again" | - |
| 1982 | W | Favorite Country Male Artist | - | - |
| 1982 | N | Favorite Country Band/Duo/Group | - | Ray Price |
| 1981 | N | Favorite Country Male Artist | - | - |
| 1980 | N | Favorite Country Male Artist | - | - |
| 1979 | N | Favorite Country Band/Duo/Group | - | Waylon Jennings |
| 1977 | W | Favorite Country Single | "Blue Eyes Cryin' in the Rain" | - |
| 1977 | N | Favorite Country Album | "Red Headed Stranger" | - |
| 1976 | N | Favorite Country Single | "Blue Eyes Cryin' in the Rain" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2004 | N | Austin Musician of the Year | - | - |
| 2003 | N | Best Austin Musicians [Acoustic Guitar] | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2004 | W | Video Collaboration of the Year | "Beer For My Horses" | Toby Keith |
| 2002 | W | Video Collaboration of the Year | "Mendocino County Line" | Lee Ann Womack |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2014 | N | CMT Performance of the Year | "Long May You Run" | Neil Young |
| 2008 | N | Wide Open Country Video of the Year | "Gravedigger" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2017 | W | Musical Event of the Year | "Funny How Time Slips Away" | Glen Campbell |
| 2015 | N | Musical Event of the Year | "Django and Jimmie" | Merle Haggard |
| 2012 | N | Musical Event of the Year | "Roll Me Up and Smoke Me When I Die" | Snoop Dogg, Kris Kristofferson, Jamey Johnson |
| 2005 | N | Musical Event of the Year | "I'll Never Be Free" | Lee Ann Womack |
| 2003 | N | Music Video of the Year | "Beer For My Horses" | - |
| 2003 | N | Vocal Event of the Year | "Beer For My Horses" | Toby Keith |
| 2003 | N | Single of the Year | "Beer For My Horses" | - |
| 2002 | W | Vocal Event of the Year | "Mendocino County Line" | Lee Ann Womack |
| 2002 | N | Album of the Year | "The Great Devide" | - |
| 1994 | N | Album of the Year | "Asleep at the Wheel Tribute to the Music of Bob Wills & the Texas Playboys" | - |
| 1991 | N | Vocal Event of the Year | "Highwaymen" | Kris Kristofferson, Johnny Cash, Waylon Jennings |
| 1990 | N | Vocal Event of the Year | "Highwaymen" | Willie Nelson, Kris Kristofferson, Johnny Cash, Waylon Jennings |
| 1990 | N | Vocal Event of the Year | - | Emmylou Harris |
| 1986 | N | Vocal Duo of the Year | - | Waylon Jennings |
| 1986 | N | Entertainer of the Year | - | - |
| 1985 | N | Single of the Year | "Highwayman" | Waylon Jennings, Kris Kristofferson, Johnny Cash |
| 1985 | N | Music Video of the Year | "Highwayman" | - |
| 1985 | N | Vocal Duo of the Year | - | Ray Charles |
| 1984 | W | Vocal Duo of the Year | - | Julio Iglesias |
| 1984 | N | Single of the Year | "To All The Girls I've Ever Loved Before" | Julio Iglesias |
| 1983 | W | Vocal Duo of the Year | - | Merle Haggard |
| 1983 | N | Single of the Year | "Pancho And Lefty" | Merle Haggard |
| 1983 | N | Album of the Year | "Pancho and Lefty" | Merle Haggard |
| 1983 | N | Male Vocalist of the Year | - | - |
| 1983 | N | Entertainer of the Year | - | - |
| 1982 | W | Album of the Year | "Always on My Mind" | - |
| 1982 | W | Single of the Year | "Always On My Mind" | - |
| 1982 | N | Entertainer of the Year | - | - |
| 1982 | N | Male Vocalist of the Year | - | - |
| 1982 | N | Vocal Duo of the Year | - | Waylon Jennings |
| 1981 | N | Male Vocalist of the Year | - | - |
| 1980 | N | Entertainer of the Year | - | - |
| 1980 | N | Male Vocalist of the Year | - | - |
| 1979 | W | Entertainer of the Year | - | - |
| 1979 | N | Vocal Duo of the Year | - | Waylon Jennings |
| 1979 | N | Male Vocalist of the Year | - | - |
| 1979 | N | Album of the Year | "One For the Road" | Leon Russell |
| 1978 | N | Album of the Year | "Waylon And Willie" | Waylon Jennings |
| 1978 | N | Vocal Duo of the Year | - | Waylon Jennings |
| 1978 | N | Male Vocalist of the Year | - | - |
| 1978 | N | Single of the Year | "Mamas Don't Let Your Babies Grow Up To Be Cowboys" | Waylon Jennings |
| 1977 | N | Vocal Duo of the Year | - | Waylon Jennings |
| 1976 | W | Vocal Duo of the Year | - | Waylon Jennings |
| 1976 | W | Single of the Year | "Good Hearted Woman" | - |
| 1976 | W | Album of the Year | "Wanted - the Outlaws" | - |
| 1976 | N | Male Vocalist of the Year | - | - |
| 1976 | N | Entertainer of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1988 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2022 | N | Best Traditional Pop Vocal Album | "That's Life" | - |
| 2020 | W | Best Country Solo Performance | "Ride Me Back Home" | - |
| 2019 | W | Best Traditional Pop Vocal Album | "My Way" | - |
| 2019 | N | Best American Roots Performance | "Last Man Standing" | - |
| 2017 | W | Best Traditional Pop Vocal Album | "Summertime: Willie Nelson Sings Gershwin" | - |
| 2011 | N | Best Americana Album | "Country Music" | - |
| 2010 | N | Best Americana Album | "Willie and the Wheel" | Asleep at the Wheel |
| 2010 | N | Best Pop Collaboration with Vocals | "Baby, It's Cold Outside" | Norah Jones |
| 2010 | N | Best Traditional Pop Vocal Album | "American Classic" | - |
| 2008 | W | Best Country Collaboration with Vocals | "Lost Highway" | Ray Price |
| 2007 | N | Best Country Album | "You Don't Know Me: The Songs of Cindy Walker" | - |
| 2006 | N | Best Male Country Vocal Performance | Good Ol' Boys" | - |
| 2006 | N | Best Country Collaboration with Vocals | "Dreams Come True" | Norah Jones |
| 2005 | N | Best Country Collaboration with Vocals | "Pancho & Lefty" | Merle Haggard, Toby Keith |
| 2005 | N | Best Country Vocal Performance - Male | "You Are My Flower" | - |
| 2004 | N | Best Country Album | "Live and Kickin'" | - |
| 2004 | N | Best Country Album | "Run That By Me One More Time" | Ray Price |
| 2004 | N | Best Country Collaboration with Vocals | "Beer For My Horses" | Toby Keith |
| 2003 | W | Best Country Collaboration with Vocals | "Mendocino County Line" | Lee Ann Womack |
| 2003 | N | Best Country Album | "The Great Divide" | - |
| 2002 | N | Best Country Album | "Rainbow Connection" | - |
| 2002 | N | Best Country Vocal Performance - Male | "Marie" | - |
| 2001 | N | Best Long Form Music Video | Willie Nelson at the Teatro (1998) | Wim Wenders (video director), Deepak Nayar (video producer) |
| 2000 | W | - | - | - |
| 2000 | N | Best Country Collaboration with Vocals | "Going Away Party" | Asleep at the Wheel, Manhattan Transfer |
| 1998 | N | Best Country Vocal Performance - Male | "Peach Pickin' Time Down in Georgia" | - |
| 1997 | N | Best Southern Gospel, Country Gospel or Bluegrass Gospel Album | "How Great Thou Art" | Bobbie Nelson |
| 1991 | W | - | - | - |
| 1991 | N | Best Country Collaboration with Vocals | "Highwayman 2" | Waylon Jennings, Kris Kristofferson, Johnny Cash |
| 1986 | N | Best Country Vocal Performance by a Duo or Group | "Highwayman" | Waylon Jennings, Johnny Cash, Kris Kristofferson |
| 1986 | N | Best Country Vocal Performance - Male | "Forgiving You Was Easy" | - |
| 1985 | N | Best Country Vocal Performance - Male | "City of New Orleans" | - |
| 1985 | N | Best Country Vocal Performance by a Duo or Group | "As Time Goes By" | Julio Iglesias |
| 1984 | N | Best Country Vocal Performance by a Duo or Group | "Take It to the Limit" | Waylon Jennings |
| 1984 | N | Best Country Vocal Performance by a Duo or Group | "Pancho and Lefty" | Merle Haggard |
| 1983 | W | Best Country Vocal Performance, Male | "Always On My Mind" | - |
| 1983 | N | Best Country Vocal Performance by a Duo or Group | "(Sittin' on) The Dock of the Bay" | Waylon Jennings |
| 1982 | N | Best Country Vocal Performance, Male | "Somewhere over the Rainbow" | - |
| 1981 | W | Best Country Song | "On the Road Again" | - |
| 1981 | N | Best Country Vocal Performance, Male | "On the Road Again" | - |
| 1980 | N | Best Country Vocal Performance, Male | "Whiskey River" | - |
| 1980 | N | Best Country Vocal Performance by a Duo or Group | "Heartbreak Hotel" | Leon Russell |
| 1979 | W | Best Country Vocal Performance, Male | "Georgia on My Mind" | - |
| 1979 | W | Best Country Vocal Performance By A Duo Or Group | "Mamas Don't Let Your Babies Grow Up To Be Cowboys" | Waylon Jennings |
| 1977 | N | Best Country Vocal Performance, Male | "I'd Have to Be Crazy" | - |
| 1976 | W | Best Country Vocal Performance, Male | "Blue Eyes Crying in the Rain" | - |
| 1975 | N | Best Country Vocal Performance By A Duo Or Group | "After the Fire is Gone" | Tracy Nelson |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2014 | N | Favorite Country Music Icon | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2002 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1995 | W | - | - | - |
| 1995 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1997 | W | Fictional Television Drama [For episode "Legend"] | Dr. Quinn, Medicine Woman (1993) | Jane Seymour, Joe Lando, Alan J. Levi |
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