| 100% | LITTLEBIGTOWN | 13 | "Better Man" singers who have won the Country Music Association Award for Vocal Group of the Year six times (3 wds.) |
| 88% | RASCALFLATTS | 12 | "Yours If You Want It" singers who have won the Country Music Association Award for Vocal Group of the Year six times (2 wds.) |
| 70% | ZACBROWNBAND | 12 | "My Old Man" singers who have been nominated for the Country Music Association Award for Vocal Group of the Year 14 times (3 wds.) |
| 53% | SIX | 3 | Number of times Garth Brooks has won the Country Music Association Award for Entertainer of the Year |
| 52% | LITTLEBIGTOWN | 13 | "Better Man" band nominated for the 2017 Country Music Award for Vocal Group of the Year (3 wds.) |
| 51% | LITTLEBIGTOWN | 13 | 15-Across and 54-Across band that won the 2017 Country Music Association Award for Vocal Group of the Year (3 wds.) |
| 50% | GARTH | 5 | Brooks who has won the Academy of Country Music's Entertainer of the Year award six times |
| 50% | LITTLEBIGTOWN | 13 | "Girl Crush" singers who won the 2016 CMA Award for Vocal Group of the Year: 3 wds. |
| 49% | CARLYPEARCE | 11 | "I Hope You're Happy Now" singer/songwriter who won the 2021 Country Music Association Award for Female Vocalist of the Year (2 wds.) |
| 48% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 48% | ZACBROWNBAND | 12 | "My Old Man" band nominated for the 2017 Country Music Award for Vocal Group of the Year (3 wds.) |
| 47% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 46% | CHRISSTAPLETON | 14 | "Tennessee Whiskey" singer-songwriter who won Male Vocalist of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 46% | OLDDOMINION | 11 | "One Man Band" quintet who won the 2021 CMA Award for Vocal Group of the Year (2 wds.) |
| 46% | LAINEYWILSON | 12 | "Heart Like a Truck" singer who won five awards, including Entertainer of the Year, at the 2023 Country Music Association Awards (2 wds.) |
| 46% | BILLIEEILISH | 12 | "All the Good Girls Go to Hell" singer who won the 2019 American Music Award for New Artist of the Year (2 wds.) |
| 45% | KENNYROGERS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Country Single a record five times (2 wds.) |
| 45% | GARTHBROOKS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Male Country Artist a record eight times (2 wds.) |
| 45% | REBAMCENTIRE | 12 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Female Country Artist a record 11 times (2 wds.) |
| 45% | OLDDOMINION | 11 | "One Man Band" country band who won Vocal Group of the Year at the 2020 CMAs: 2 wds. |
| 44% | CONWAYTWITTY | 12 | Country Music Hall of Fame singer who shared four consecutive CMA Awards for Vocal Duo of the Year with 28-Across in the 1970s (2 wds.) |
| 44% | JONIMITCHELL | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2001 Vocal Jazz Album of the Year Juno Award for "Both Sides Now" (2 wds.) |
| 44% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 44% | OLDDOMINION | 11 | "Written in the Sand" band that won Vocal Group of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 43% | TRACYCHAPMAN | 12 | "Fast Car" songwriter who won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 42% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 42% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 42% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 41% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 41% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |