| 100% | JENNIFERLOPEZ | 13 | "Let's Get Loud" singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| 60% | CAITLYNJENNER | 13 | Transgender rights activist who was named Glamour Woman of the Year in 2015: 2 wds. |
| 60% | GRETATHUNBERG | 13 | Swedish environmental activist who was named Glamour Woman of the Year in 2019: 2 wds. |
| 55% | TARAVANDERVEER | 14 | Stanford University women's basketball coach who was named Naismith Coach of the Year in 1990, 2011, and 2021 (2 wds.) |
| 49% | PATSUMMITT | 10 | University of Tennessee women's basketball coach who was named Naismith Coach of the Year in 1987, 1989, 1994, 1998, and 2004 (2 wds.) |
| 49% | DAWNSTALEY | 10 | University of South Carolina women's basketball coach who was named Naismith Coach of the Year in 2020, 2022, and 2023 (2 wds.) |
| 48% | ARIANAGRANDE | 12 | 17-Across and 39-Across singer who was named Billboard's 2018 Woman of the Year (2 wds.) |
| 47% | CANDACEPARKER | 13 | Chicago Sky star who was named both WNBA Rookie of the Year and WNBA MVP in 2008: 2 wds. |
| 45% | BARACKOBAMA | 11 | Political victor who was Time's Person of the Year in 2008 and 2012: 2 wds. |
| 43% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 43% | DOLLYPARTON | 11 | "Jolene" singer who was inducted into the Country Music Hall of Fame in 1999: 2 wds. |
| 42% | QUINTABRUNSON | 13 | "Abbott Elementary" creator and star who was one of Glamour's 2023 Women of the Year: 2 wds. |
| 42% | TRINITYRODMAN | 13 | Washington Spirit forward who was named 2021 National Women's Soccer League Rookie of the Year (2 wds.) |
| 42% | ARIANAGRANDE | 12 | "Positions" singer who was Billboard's 2018 Woman of the Year: 2 wds. |
| 42% | COOPERKUPP | 10 | 2021 NFL Offensive Player of the Year who caught two touchdown passes in the 2022 Super Bowl for 21-Across and was named Super Bowl MVP (2 wds.) |
| 42% | LINDARONSTADT | 13 | "You're No Good" singer who was inducted into the Rock and Roll Hall of Fame in 2014: 2 wds. |
| 41% | BILLIEEILISH | 12 | "Bad Guy" singer who was Billboard's 2019 Woman of the Year: 2 wds. |
| 41% | CHARLIZETHERON | 14 | "Monster" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2008: 2 wds. |
| 41% | CAITLINCLARK | 12 | Iowa Hawkeyes championship game scoring leader who was named AP Player of the Year and Naismith College Player of the Year in 2023 (2 wds.) |
| 41% | TONYBENNETT | 11 | 2018 AP Coach of the Year who shares his name with the singer of "I Left My Heart in San Francisco": 2 wds. |
| 41% | RINASAWAYAMA | 12 | Singer/songwriter and model who was one of "Vogue" Japan's 2019 women of the year (2 wds.) |
| 41% | JEFFLYNNE | 9 | "Evil Woman" singer who was inducted into the Songwriters Hall of Fame in 2023: 2 wds. |
| 40% | OCTAVIASPENCER | 14 | "The Help" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2017: 2 wds. |
| 40% | OLIVIARODRIGO | 13 | "Good 4 U" singer who was Billboard's 2021 Woman of the Year: 2 wds. |
| 40% | DOLLYPARTON | 11 | "Jolene" singer who was MusiCares Person of the Year in 2019: 2 wds. |
| 40% | RENEEZELLWEGER | 14 | "Cold Mountain" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2009: 2 wds. |
| 40% | ERICCLAPTON | 11 | "Layla" guitarist and singer who was inducted into the Rock and Roll Hall of Fame in 2000: 2 wds. |
| 40% | SANDRABULLOCK | 13 | Actress who was EW's only two-time Entertainer of the Year, in 2009 and 2013: 2 wds. |
| 39% | JOHNLEGEND | 10 | "All of Me" singer and "The Voice" coach who was named People's Sexiest Man Alive in 2019: 2 wds. |
| 39% | MARENMORRIS | 11 | 1-Across, 12-Across, 27-Across, and 50-Across country/pop singer who was named Female Vocalist of the Year by the Country Music Association in 2020 (2 wds.) |