| 100% | OLDDOMINION | 11 | "Written in the Sand" band that won Vocal Group of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 68% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 67% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 62% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 59% | OLDDOMINION | 11 | "One Man Band" country band who won Vocal Group of the Year at the 2020 CMAs: 2 wds. |
| 58% | LITTLEBIGTOWN | 13 | 15-Across and 54-Across band that won the 2017 Country Music Association Award for Vocal Group of the Year (3 wds.) |
| 49% | RASCALFLATTS | 12 | "Yours If You Want It" band nominated for the 2017 Country Music Award for Vocal Group of the Year (2 wds.) |
| 48% | FASTCAR | 7 | 1988 Tracy Chapman hit that won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 48% | KNOWINGYOU | 10 | Top 10 single that 30-Across performed at the Academy of Country Music Awards ceremony in 2021 (2 wds.) |
| 48% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 48% | CHRISSTAPLETON | 14 | "Tennessee Whiskey" singer-songwriter who won Male Vocalist of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 47% | LITTLEBIGTOWN | 13 | "Better Man" band nominated for the 2017 Country Music Award for Vocal Group of the Year (3 wds.) |
| 47% | OLDDOMINION | 11 | "One Man Band" quintet who won the 2021 CMA Award for Vocal Group of the Year (2 wds.) |
| 47% | TRACYCHAPMAN | 12 | "Fast Car" songwriter who won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 47% | ZACBROWNBAND | 12 | "My Old Man" band nominated for the 2017 Country Music Award for Vocal Group of the Year (3 wds.) |
| 47% | 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.) |
| 47% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 46% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 46% | KILLINTIME | 10 | Album by 45-Across featuring the singles 18-Across and 26-Across that won the 1989 Album of the Year Academy of Country Music Award (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.) |
| 45% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 45% | LITTLEBIGTOWN | 13 | "Better Man" singers who have won the Country Music Association Award for Vocal Group of the Year six times (3 wds.) |
| 45% | WASTED | 6 | Carrie Underwood song that won Most Performed Song of the Year in the 2007 ASCAP Country Music Awards |
| 45% | ABETTERMAN | 10 | #1 song by 45-Across from 35-Across that won the 1989 Single of the Year Academy of Country Music Award (3 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.) |
| 43% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 42% | DIERKSBENTLEY | 13 | Singer of 15-Across and 29-Across who was awarded the 2018 Academy of Country Music's Merle Haggard Spirit Award (2 wds.) |
| 42% | MISSYFRANKLIN | 13 | Five-time Olympic swimming gold medalist who won Female Athlete of the Year at the 2011 and 2012 Golden Goggle Awards: 2 wds. |
| 42% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 42% | 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.) |