| 100% | LAINEYWILSON | 12 | 2021 Academy of Country Music Awards New Artist of the Year who sings 30-Across with 40-Across (2 wds.) |
| 87% | COLESWINDELL | 12 | 2015 Academy of Country Music Awards New Artist of the Year who sings 30-Across with 18-Across (2 wds.) |
| 50% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 49% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (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% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 48% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 47% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 47% | DOJACAT | 7 | 13-Across, 19-Across, and 38-Across singer who was named New Artist of the Year at the 2020 American Music Awards (2 wds.) |
| 46% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 46% | BRETTELDREDGE | 13 | "Lose My Mind" singer who won the 2014 CMA New Artist of the Year award: 2 wds. |
| 46% | TAYLORSWIFT | 11 | "Shake It Off" singer who won the 2007 CMA New Artist of the Year award: 2 wds. |
| 45% | KEITHURBAN | 10 | "Blue Ain't Your Color" singer who hosted the socially distant 2020 Academy of Country Music Awards: 2 wds. |
| 45% | 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% | HARRYSTYLES | 11 | "As It Was" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |
| 44% | TAYLORSWIFT | 11 | "Anti-Hero" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |
| 43% | DUALIPA | 7 | "Cold Heart" singer who, with Elton John, won the 2022 American Music Award for Collaboration of the Year (2 wds.) |
| 43% | ASHLEYMCBRYDE | 13 | "Girl Going Nowhere" singer who won the 2019 CMA Award for New Artist of the Year (2 wds.) |
| 43% | JUSTINBIEBER | 12 | 2010 American Music Awards New Artist of the Year whose fifth studio album, "Changes," debuted at #1 on the U.S. "Billboard" 200 in 2020 (2 wds.) |
| 43% | ARIANAGRANDE | 12 | 2013 American Music Awards New Artist of the Year whose sixth studio album, "Positions," debuted at #1 on the U.S. "Billboard" 200 in 2020 (2 wds.) |
| 43% | 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.) |
| 43% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 43% | JONASBROTHERS | 13 | 2008 American Music Awards New Artist of the Year whose fifth studio album, "Happiness Begins," debuted at #1 on the U.S. "Billboard" 200 in 2019 (2 wds.) |
| 42% | 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.) |
| 42% | TRACYCHAPMAN | 12 | "Fast Car" songwriter who won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 42% | OLDDOMINION | 11 | "Written in the Sand" band that won Vocal Group of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 42% | CHRISSTAPLETON | 14 | "Tennessee Whiskey" singer-songwriter who won Male Vocalist of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 41% | 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.) |
| 41% | DIERKSBENTLEY | 13 | Singer of 15-Across and 29-Across who was honored with an Academy of Country Music's Merle Haggard Spirit Award (2 wds.) |
| 41% | IVAN | 4 | Cornejo who won New Artist of the Year at the 2022 Billboard Latin Music Awards |