| 100% | CYNDILAUPER | 11 | "Time After Time" singer who was honored with the "Billboard" Women in Music Icon Award in 2018 (2 wds.) |
| 81% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who was honored with the "Billboard" Women in Music Icon Award in 2020 (2 wds.) |
| 81% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who was honored with the "Billboard" Women in Music Icon Award in 2016 (2 wds.) |
| 67% | DEBBIEHARRY | 11 | Lead singer of Blondie who received the first Billboard Women in Music Icon Award, in 2008: 2 wds. |
| 65% | JANETJACKSON | 12 | "Rhythm Nation" singer who was honored with a "Billboard" Icon Award in 2018 (2 wds.) |
| 64% | CYNDILAUPER | 11 | "Girls Just Want to Have Fun" singer who received the Billboard Women in Music Icon Award in 2018: 2 wds. |
| 62% | JENNIFERLOPEZ | 13 | 15-Across and 27-Across singer who was the first woman honored with a "Billboard" Icon Award (2 wds) |
| 60% | KYLIEMINOGUE | 12 | "Padam Padam" singer who received the Billboard Women in Music Icon Award in 2024: 2 wds. |
| 59% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who received the Billboard Women in Music Icon Award in 2020: 2 wds. |
| 59% | BONNIERAITT | 11 | "Something to Talk About" singer who received the Billboard Women in Music Icon Award in 2021: 2 wds. |
| 59% | ANDERSONCOOPER | 14 | CNN host who was honored with the 2018 Walter Cronkite Award for Excellence in Journalism (2 wds.) |
| 58% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who received the Billboard Women in Music Icon Award in 2016: 2 wds. |
| 58% | STEVIEWONDER | 12 | "For Once in My Life" singer who was honored with a "Billboard" Icon Award in 2012 (2 wds.) |
| 56% | MARYJBLIGE | 10 | "Be Without You" singer who was honored with a "Billboard" Icon Award in 2022 (3 wds.) |
| 55% | SOLANGEKNOWLES | 14 | 12-Across and 28-Across singer who was the first recipient of the "Billboard" Women in Music Impact Award (2 wds.) |
| 55% | JANELLEMONAE | 12 | "Dirty Computer" pop funk singer who was honored with the 2023 Soul Train Spirit of Soul Award: 2 wds. |
| 55% | YOLANDAADAMS | 12 | "Be Blessed" gospel singer who was honored with the 2019 Soul Train Lady of Soul Award: 2 wds. |
| 54% | HELENMIRREN | 11 | "The Queen" Oscar winner who was honored with Lincoln Center's Chaplin Award in 2018: 2 wds. |
| 54% | MARIOLEMIEUX | 12 | Pittsburgh Penguins center who was honored with the Best NHL Player ESPY Award three times: 2 wds. |
| 54% | SIDNEYCROSBY | 12 | Pittsburgh Penguins center who was honored with the Best NHL Player ESPY Award eight times: 2 wds. |
| 52% | ROBINROBERTS | 12 | "Good Morning America" co-anchor who was honored with the 2014 Walter Cronkite Award for Excellence in Journalism (2 wds.) |
| 51% | KALIUCHIS | 9 | 15-Across and 32-Across singer-songwriter who was honored as the Top Latin Female Artist at the 2022 Billboard Music Awards (2 wds.) |
| 51% | ARIANAGRANDE | 12 | "Positions" singer who was Billboard's 2018 Woman of the Year: 2 wds. |
| 50% | ELTONJOHN | 9 | Singer who was honored with the Ben & Jerry's flavor Goodbye Yellow Brickle Road: 2 wds. |
| 50% | TAYLORSWIFT | 11 | "Anti-Hero" singer who was honored with the People's Choice Award for The Female Artist of 2022 (2 wds.) |
| 50% | MARIAHCAREY | 11 | "Emotions" singer who received the Billboard Icon Award in 2019: 2 wds. |
| 50% | HARRYSTYLES | 11 | "As It Was" singer who was honored with the People's Choice Award for The Male Artist of 2022 (2 wds.) |
| 49% | NEILDIAMOND | 11 | "Sweet Caroline" singer who received the Billboard Icon Award in 2011: 2 wds. |
| 49% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was honored with the 1972 Grammy Award for Best Male Country Vocal Performance (2 wds.) |
| 49% | JONIMITCHELL | 12 | 15-Across and 44-Across singer-songwriter who was honored with a Gershwin Award in 2023 (2 wds.) |