(*): W=Win, N=Nomination
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1993 | W | Favorite New Adult Contemporary Artist | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2018 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1995 | W | Best International Female | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2009 | W | Outstanding Music Artist | "Watershed" | - |
| 2003 | W | Outstanding Music Album | "A Wonderful World" | Tony Bennett |
| 2001 | W | Outstanding Music Album | "Invincible Summer" | - |
| 1998 | W | - | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2004 | W | Best Traditional Pop Vocal Album | "A Wonderful World" | Tony Bennett |
| 2004 | N | Best Pop Collaboration with Vocals | "La Vie En Rose" | Tony Bennett |
| 2003 | N | Best Pop Collaboration with Vocals | "What a Wonderful World" | Tony Bennett |
| 1995 | N | Best Pop Collaboration with Vocals | "Moonglow" | Tony Bennett |
| 1994 | N | Best Pop Vocal Performance - Female | "Miss Chatelaine" | - |
| 1993 | W | Best Pop Vocal Performance - Female | "Constant Craving" | - |
| 1993 | N | Song of the Year | "Constant Craving" | Ben Mink (Co-songwriter) |
| 1993 | N | Record of the Year | "Constant Craving" | - |
| 1993 | N | Album of the Year | "Ingenue" | - |
| 1990 | W | Best Country Vocal Performance - Female | "Absolute Torch and Twang" | - |
| 1990 | N | Best Country Vocal Collaboration | "Sin City" | Dwight Yoakam |
| 1990 | N | Best Country Song | "Luck in My Eyes" | Ben Mink (Co-songwriter) |
| 1989 | W | Best Country Vocal Collaboration | "Crying" | Roy Orbison |
| 1989 | N | Best Country Vocal Performance - Female | "I'm Down to My Last Cigarette" | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2013 | W | Canadian Music Hall of Fame | - | - |
| 2009 | N | Jack Richardson Producer of the Year | "I Dream of Spring"; "Coming Home" | - |
| 2009 | N | Artist of the Year | - | - |
| 2005 | N | Artist of the Year | - | - |
| 1994 | N | Producer of the Year | "Just Keep Me Moving" | Ben Mink |
| 1993 | W | Album of the Year | "Ingenue" | - |
| 1993 | W | Songwriter of the Year | - | Ben Mink |
| 1993 | W | Producer of the Year | "Constant Craving"; "The Mind of Love" | Ben Mink |
| 1993 | N | Female Vocalist of the Year | - | - |
| 1990 | W | Country Female Vocalist of the Year | - | - |
| 1990 | N | Canadian Entertainer of the Year | - | - |
| 1989 | W | Female Vocalist of the Year | - | - |
| 1989 | W | Country Female Vocalist of the Year | - | - |
| 1989 | N | Canadian Entertainer of the Year | - | - |
| 1987 | W | Country Female Vocalist of the Year | - | - |
| 1987 | N | Female Vocalist of the Year | - | - |
| 1987 | N | Canadian Entertainer of the Year | - | - |
| 1985 | W | Most Promising Female Vocalist of the Year | - | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1993 | W | Best Female Video | "Constant Craving" | - |
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