Awards and Nominations
| Year | Association | Category | Result |
|---|---|---|---|
| 1997 | Country Music Association Awards | Single of the Year — "Strawberry Wine" | Won |
| Song of the Year — "Strawberry Wine" | Nominated | ||
| Female Vocalist of the Year | Nominated | ||
| Horizon Award | Nominated | ||
| Album of the Year — Did I Shave My Legs for This? | Nominated | ||
| Music Video of the Year — "Strawberry Wine" | Nominated | ||
| 1998 | Academy of Country Music Awards | Single Record of the Year — "Strawberry Wine" | Nominated |
| Song of the Year — "Strawberry Wine" | Nominated | ||
| Top New Female Vocalist | Nominated | ||
| Country Music Association Awards | Music Video of the Year — "Did I Shave My Legs for This?" | Nominated | |
| 39th Grammy Awards | Best Country Female Vocal Performance — "Strawberry Wine" | Nominated | |
| 2011 | Country Music Association Awards | Song of the Year — "You and Tequila" | Nominated |
| 2012 | 54th Grammy Awards | Best Country Song — "You and Tequila" | Nominated |
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