| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2005 | W | Female Vocalist of the Year | - | - |
| 2005 | W | Songwriter of the Year | "Narrow Daylight" | Elvis Costello |
| 2005 | W | Album of the Year | "The Girl in the Other Room" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2008 | N | National/International Jazz Production of the Year | "The Very Best of Diana Krall" | - |
| 2007 | N | National/International Jazz Production of the Year | "From This Moment On" | - |
| 2006 | N | National/International Jazz Production of the Year | "Christmas Songs" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2019 | N | Best Pop Duo/Group Performance | "'S Wonderful" | Tony Bennett |
| 2019 | N | Best Traditional Pop Vocal Album | "Love Is Here to Stay" | Tony Bennett |
| 2007 | N | Best Jazz Vocal Album | "From This Moment On" | - |
| 2003 | W | Best Jazz Vocal Album | "Live In Paris" | - |
| 2003 | N | Best Pop Collaboration With Vocals | "Better Than Anything" | Natalie Cole |
| 2000 | W | Best Jazz Vocal Performance | "When I Look In Your Eyes" | - |
| 2000 | N | Album of the Year | "When I Look in Your Eyes" | - |
| 1998 | N | Best Jazz Vocal Performance | "Love Scenes" | - |
| 1997 | N | Best Jazz Vocal Performance | "All for You" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2019 | N | Vocal Jazz Album of the Year | "Love Is Here to Stay" | Tony Bennett |
| 2018 | W | Jack Richardson Producer of the Year | "Turn Up the Quiet" | Tommy Lipuma |
| 2018 | W | Vocal Jazz Album of the Year | "Turn Up the Quiet" | - |
| 2016 | N | Adult Contemporary Album of the Year | "Wallflower" | - |
| 2010 | W | Vocal Jazz Album of the Year | "Quiet Nights" | - |
| 2010 | N | Album of the Year | "Quiet Nights" | - |
| 2010 | N | Artist of the Year | - | - |
| 2007 | W | Vocal Jazz Album of the Year | "From This Moment On" | - |
| 2007 | N | Artist of the Year | - | - |
| 2006 | W | Vocal Jazz Album of the Year | "Christmas Songs" | - |
| 2006 | N | Artist of the Year | - | - |
| 2006 | N | Album of the Year | "Christmas Songs" | - |
| 2006 | N | - | - | - |
| 2005 | W | Vocal Jazz Album of the Year | "The Girl In The Other Room" | - |
| 2005 | N | - | - | - |
| 2005 | N | Artist of the Year | - | - |
| 2005 | N | Album of the Year | "The Girl In The Other Room" | - |
| 2003 | W | Vocal Jazz Album of the Year | "Live In Paris" | - |
| 2003 | N | - | - | - |
| 2002 | W | Best Artist | - | - |
| 2002 | W | Best Vocal Jazz Album | "The Look of Love" | - |
| 2002 | W | Best Album | "The Look of Love" | - |
| 2000 | W | Best Vocal Jazz Album | "When I Look In Your Eyes" | - |
| 1998 | N | Best Mainstream Jazz Album | "Love Scenes" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2009 | N | Best Jazz Act | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2007 | W | Female Vocalist of the Year | - | - |
| 2007 | W | International Musician of the Year | - | - |
| 2004 | W | International Musician of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2003 | W | Vocalist of the Year | - | - |
| 2003 | W | Vocal Song of the Year | "The Look of Love" | - |
| 2003 | W | Female Artist of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2005 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1998 | W | Best Jazz Album | "Love Scenes" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2005 | W | Outstanding Album (Major Label) | "The Girl in the Other Room" | - |
| 2005 | N | Entertainer of the Year | - | - |
| 2005 | N | Outstanding Jazz Recording | "The Girl in the Other Room" | - |