(*): W=Win, N=Nomination
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2017 | W | - | - | - |
| 2015 | W | - | - | - |
| 2014 | W | Entertainer of the Year | - | - |
| 2011 | N | Top Male Vocalist of the Year | - | - |
| 2010 | N | Top Male Vocalist of the Year | - | - |
| 2010 | N | Entertainer of the Year | - | - |
| 2009 | N | Entertainer of the Year | - | - |
| 2009 | N | Top Male Vocalist | - | - |
| 2009 | N | Song of the Year | "I Saw God Today" | - |
| 2009 | N | Video of the Year | "Troubadour" | - |
| 2009 | N | Album of the Year | "Troubadour" | - |
| 2008 | N | Vocal Event of the Year | "Shiftwork" | Kenny Chesney |
| 2008 | N | Top Male Vocalist | - | - |
| 2008 | N | Entertainer of the Year | - | - |
| 2007 | W | Song of the Year | "Give It Away" | Bill Anderson, Buddy Cannon, Jamey Johnson (songwriters) |
| 2007 | W | Single Record of the Year | "Give It Away" | - |
| 2007 | N | Video of the Year | "Seashores of Old Mexico" | - |
| 2007 | N | Album of the Year | "It Just Comes Natural" | - |
| 2007 | N | Top Male Vocalist | - | - |
| 2007 | N | Entertainer of the Year | - | - |
| 2006 | N | Top Male Vocalist | - | - |
| 2003 | W | Career Achievement | - | - |
| 1997 | W | Top Male Vocalist | - | - |
| 1997 | W | Album of the Year | "Carrying Your Love With Me " | - |
| 1996 | W | Top Male Vocalist | - | - |
| 1996 | W | Album of the Year | "Blue Clear Sky " | - |
| 1989 | W | Entertainer of the Year | - | - |
| 1988 | W | Top Male Vocalist | - | - |
| 1985 | W | Top Male Vocalist | - | - |
| 1985 | W | Album of the Year | "Does Fort Worth Ever Cross Your Mind " | - |
| 1984 | W | Male Vocalist of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1993 | W | Pure Country | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2011 | N | Touring Headline Act of the Year | - | - |
| 2010 | N | Touring Headline Package of the Year | - | Reba McEntire |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2000 | N | Favorite Country Album | "Always Never The Same" | - |
| 2000 | N | Favorite Country Male Artist | - | - |
| 1999 | N | Favorite Country Album | "One Step At A Time" | - |
| 1999 | N | Favorite Country Male Artist | - | - |
| 1998 | W | Favorite Country Album | "Carrying Your Love With Me" | - |
| 1998 | W | Favorite Country Male Artist | - | - |
| 1997 | W | Favorite Album | "Blue Clear Sky " | - |
| 1997 | N | Favorite Country Male Artist | - | - |
| 1996 | N | Favorite Country Male Artist | - | - |
| 1991 | W | Favorite Male Artist | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2020 | W | Top Country Tour | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2009 | W | CMT Performance of the Year | "Country Boy" | Alan Jackson, Brad Paisley, Dierks Bentley |
| 2007 | N | Video of the Year | "The Seashores of Old Mexico" | - |
| 2005 | N | Collaborate Video of the Year | "Hey Good Lookin" | Jimmy Buffett, Kenny Chesney, Toby Keith, Clint Back, Alan Jackson |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2014 | N | Entertainer of the Year | - | - |
| 2013 | W | Entertainer of the Year | - | - |
| 2010 | N | Album of the Year | "Twang" | - |
| 2010 | N | Male Vocalist | - | - |
| 2009 | N | Music Video of the Year | "Troubadour" | - |
| 2009 | N | Musical Event of the Year | "Everything But Quits" | Lee Ann Womack |
| 2009 | N | Male Vocalist of the Year | - | - |
| 2009 | N | Entertainer of the Year | - | - |
| 2008 | W | Single of the Year | "I Saw God Today" | - |
| 2008 | W | Album of the Year | "Troubadour" | - |
| 2008 | N | Musical Event of the Year | "Shiftwork" | Kenny Chesney |
| 2008 | N | Male Vocalist of the Year | - | - |
| 2008 | N | Entertainer of the Year | - | - |
| 2007 | W | Album of the Year | "It Just Comes Natural" | - |
| 2007 | N | Entertainer of the Year | - | - |
| 2007 | N | Male Vocalist of the Year | - | - |
| 2007 | N | Single of the Year | "Wrapped" | - |
| 2007 | N | Musical Event of the Year | "Hey Good Lookin" (Live) | Jimmy Buffett, Alan Jackson |
| 2005 | W | Musical Event of the Year | "Good News, Bad News" | Lee Ann Womack |
| 2005 | N | Album of hte Year | "Somewhere Down In Texas" | - |
| 2005 | N | Male Vocalist of the Year | - | - |
| 2000 | W | Vocal Event of the Year | "Murder on Music Row" | Alan Jackson |
| 1998 | W | Male Vocalist of the Year | - | - |
| 1997 | W | Album of the Year | "Carrying Your Love With Me" | - |
| 1997 | W | Male Vocalist of the Year | - | - |
| 1996 | W | Male Vocalist of the Year | - | - |
| 1996 | W | Single of the Year | "Check Yes Or No" | - |
| 1990 | W | Entertainer of the Year | - | - |
| 1989 | W | Entertainer of the Year | - | - |
| 1986 | W | Male Vocalist of the Year | - | - |
| 1985 | W | Male Vocalist of the Year | - | - |
| 1985 | W | Album of the Year | "Does Fort Worth Ever Cross Your Mind" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1997 | W | Favorite Video Entertainer | - | - |
| 1997 | W | Favorite Video | "Check Yes Or No" | - |
| 1997 | W | Favorite Album | "Blue Clear Sky" | - |
| 1996 | W | Favorite Song | "Check Yes Or No" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2000 | W | Album of the Year | "Always Never The Same" | - |
| 2000 | W | Entertainer of the Year | - | - |
| 2000 | W | Male Artist of the Year | - | - |
| 2000 | W | Single of the Year | "Write This Down" | - |
| 2000 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2012 | N | Best Country Album | "Here for a Good Time" | - |
| 2010 | N | Best Country Album | "Twang" | - |
| 2010 | N | Best Country Collaboration with Vocals | "Everything But Quits" | Lee Ann Womack |
| 2010 | N | Best Male Country Vocal Performance | "Living for the Night" | - |
| 2009 | W | Best Country Album | "Troubadour" | - |
| 2009 | N | Best Male Country Vocal Performance | "Troubadour" | - |
| 2009 | N | Best Country Collaboration with Vocals | "Shiftwork" | Kenny Chesney |
| 2009 | N | Best Country Collaboration with Vocals | "House of Cash" | Patty Loveless |
| 2008 | N | Best Country Album | "It Just Comes Natural" | - |
| 2008 | N | Best Male Country Vocal Performance | "Give It Away" | - |
| 2007 | N | Best Country Vocal Performance - Male | "The Seashores of Old Mexico" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2008 | W | Mainstream Inspirational Song of the Year | "I Saw God Today" | - |
| 2008 | N | Mainstream Country Artist of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1986 | W | Male Artist of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2014 | N | Favorite Country Music Icon | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2005 | N | Artist of the Year/Country Radio | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1999 | W | Album of the Year | "One Step at a Time" | - |
| 1997 | W | Album of the Year | "Blue Clear Sky" | - |
| 1996 | W | Album of the Year | "Lead On" | - |
| 1996 | W | Single of the Year | "Check Yes Or No" | - |
| 1996 | W | Video of the Year | "Check Yes Or No" | - |
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