| 100% | LITTLEBIGTOWN | 13 | 15-Across and 54-Across band that won the 2017 Country Music Association Award for Vocal Group of the Year (3 wds.) |
| 60% | 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.) |
| 59% | LITTLEBIGTOWN | 13 | "Better Man" band nominated for the 2017 Country Music Award for Vocal Group of the Year (3 wds.) |
| 59% | ZACBROWNBAND | 12 | "My Old Man" band nominated for the 2017 Country Music Award for Vocal Group of the Year (3 wds.) |
| 59% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 56% | OLDDOMINION | 11 | "Written in the Sand" band that won Vocal Group of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 56% | LITTLEBIGTOWN | 13 | "Better Man" singers who have won the Country Music Association Award for Vocal Group of the Year six times (3 wds.) |
| 56% | RASCALFLATTS | 12 | "Yours If You Want It" band nominated for the 2017 Country Music Award for Vocal Group of the Year (2 wds.) |
| 54% | 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.) |
| 53% | 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.) |
| 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.) |
| 45% | LITTLEBIGTOWN | 13 | "Girl Crush" singers who won the 2016 CMA Award for Vocal Group of the Year: 3 wds. |
| 45% | OLDDOMINION | 11 | "One Man Band" quintet who won the 2021 CMA Award for Vocal Group of the Year (2 wds.) |
| 45% | FASTCAR | 7 | 1988 Tracy Chapman hit that won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 44% | 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% | GIRL | 4 | 2019 album by 44-Across that won the Country Music Association's Album of the Year Award |
| 44% | LUKASGRAHAM | 11 | Danish pop and soul band with the hit single "7 Years", that was nominated for Record of the Year in the 2017 Grammy Awards : 2 wds. |
| 44% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 44% | AHARDDAYS | 9 | "___ Night," a musical comedy film starring the Beatles that won 31-Across an Academy Award for scoring of music: 3 wds. |
| 42% | TRACYCHAPMAN | 12 | "Fast Car" songwriter who won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 41% | POSTMALONE | 10 | 18-Across, 27-Across, and 34-Across rapper whose "Rockstar" won the 2018 Billboard Music Award for Top Rap Song and the 2018 MTV Video Music Award for Song of the Year (2 wds.) |
| 41% | RAIN | 4 | "___ On Me," song by Lady Gaga and Ariana Grande that won the MTV Video Music Award for Song of the Year in 2020 |
| 41% | MENATWORK | 9 | 15-Across and 33-Across rock band from Australia that won Best New Artist at the 1983 Grammy Awards (3 wds.) |
| 41% | PERRY | 5 | The Band ___, country music group that won a Grammy for their cover of the song "Gentle on My Mind" |
| 41% | 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.) |
| 41% | YOUMIGHTTHINK | 13 | The Cars Top 10 hit whose video features 44-Across as a housefly (and was the first to win the MTV Video Music Award for Video of the Year) (3 wds.) |
| 41% | CHRISSTAPLETON | 14 | "Tennessee Whiskey" singer-songwriter who won Male Vocalist of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 41% | KISSMEKATE | 10 | 1948 show with music and lyrics by 39-Across that won the first Tony Award for Best Musical (3 wds.) |
| 41% | 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.) |
| 41% | SIX | 3 | Number of times Garth Brooks has won the Country Music Association Award for Entertainer of the Year |