| 100% | JENNIFERLOPEZ | 13 | 15-Across and 27-Across singer who was the first woman honored with a "Billboard" Icon Award (2 wds) |
| 60% | CYNDILAUPER | 11 | "Time After Time" singer who was honored with the "Billboard" Women in Music Icon Award in 2018 (2 wds.) |
| 60% | JONIMITCHELL | 12 | 15-Across and 44-Across singer-songwriter who was honored with a Gershwin Award in 2023 (2 wds.) |
| 60% | SOLANGEKNOWLES | 14 | 12-Across and 28-Across singer who was the first recipient of the "Billboard" Women in Music Impact Award (2 wds.) |
| 59% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who was honored with the "Billboard" Women in Music Icon Award in 2020 (2 wds.) |
| 59% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who was honored with the "Billboard" Women in Music Icon Award in 2016 (2 wds.) |
| 58% | 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.) |
| 57% | SELMALAGERLOF | 13 | Swedish novelist and short story writer who was the first woman honored with the Nobel Prize in Literature (2 wds.) |
| 55% | JANETJACKSON | 12 | "Rhythm Nation" singer who was honored with a "Billboard" Icon Award in 2018 (2 wds.) |
| 54% | STEVIEWONDER | 12 | "For Once in My Life" singer who was honored with a "Billboard" Icon Award in 2012 (2 wds.) |
| 54% | TAYLORSWIFT | 11 | Multiple Grammy-winning singer-songwriter who is the first-ever recipient of Billboard's Woman of the Decade Award: 2 wds. |
| 53% | DEBBIEHARRY | 11 | Lead singer of Blondie who received the first Billboard Women in Music Icon Award, in 2008: 2 wds. |
| 53% | BABERUTH | 8 | 15-Across great known as the "Sultan of Swat" who was honored with a "Day" at Yankee Stadium on April 27, 1947 (2 wds.) |
| 52% | 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.) |
| 52% | MARYJBLIGE | 10 | "Be Without You" singer who was honored with a "Billboard" Icon Award in 2022 (3 wds.) |
| 51% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was the first Black country artist to cohost the CMA Awards (1975) and the ACM Awards (1980): 2 wds. |
| 51% | WHOOPIGOLDBERG | 14 | Actress and comedian who was the first woman awarded the 44-Across (2001) (2 wds.) |
| 51% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 51% | JOCELYNALO | 10 | Softball player who won two National Championships with the Oklahoma Sooners and who was honored with a Best College Athlete, Women's Sports ESPY Award in 2022 (2 wds.) |
| 51% | KYLIEMINOGUE | 12 | "Padam Padam" singer who received the Billboard Women in Music Icon Award in 2024: 2 wds. |
| 51% | DRAKE | 5 | Singer of 15-Across, 28-Across, and 38-Across who was honored with the Artist of the Decade Award at the 2021 "Billboard" Music Awards |
| 51% | EDITHWHARTON | 12 | 13-Across and 25-Across writer who was the first woman to win a Pulitzer Prize in Literature, for her 1920 novel "The Age of Innocence" (2 wds.) |
| 50% | BONNIERAITT | 11 | "Something to Talk About" singer who received the Billboard Women in Music Icon Award in 2021: 2 wds. |
| 50% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who received the Billboard Women in Music Icon Award in 2020: 2 wds. |
| 50% | CYNDILAUPER | 11 | "Girls Just Want to Have Fun" singer who received the Billboard Women in Music Icon Award in 2018: 2 wds. |
| 50% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who received the Billboard Women in Music Icon Award in 2016: 2 wds. |
| 50% | SINCLAIRLEWIS | 13 | Minnesota novelist and short story writer who was the first American honored with the Nobel Prize in Literature (2 wds.) |
| 50% | ARIANAGRANDE | 12 | 17-Across and 39-Across singer who was named Billboard's 2018 Woman of the Year (2 wds.) |
| 49% | WOLESOYINKA | 11 | Nigerian playwright and novelist who was the first African honored with the Nobel Prize in Literature (2 wds.) |
| 49% | HARLANCOBEN | 11 | 17-Across and 30-Across novelist who is the first writer to win an Anthony Award, a Shamus Award, and an Edgar Award (2 wds.) |