| 100% | JOHNDILLINGER | 13 | Depression-era gangster who was the FBI's first "Public Enemy #1": 2 wds. |
| 49% | MARGARETCOURT | 13 | Australian tennis player who was the first woman to win the Grand Slam in the Open Era: 2 wds. |
| 45% | JACKIESTILES | 12 | 2016 Women's Basketball Hall of Fame inductee who was the first Division I player to score over 1,000 points in a season: 2 wds. |
| 44% | MARIECURIE | 10 | Scientist who was the first female professor at the University of Paris: 2 wds. |
| 44% | JENNADEWAN | 10 | "Step Up" actress who was the first host of "World of Dance": 2 wds. |
| 44% | DONNYOSMOND | 11 | Actor who was the Peacock on season 1 of "The Masked Singer": 2 wds. |
| 44% | TORISPELLING | 12 | Actress who was the Unicorn on season 1 of "The Masked Singer": 2 wds. |
| 44% | MARGARETCHO | 11 | Comedian who was the Poodle on season 1 of "The Masked Singer": 2 wds. |
| 44% | TAYLORSWIFT | 11 | Multiple Grammy-winning singer-songwriter who is the first-ever recipient of Billboard's Woman of the Decade Award: 2 wds. |
| 44% | CANDICEBERGEN | 13 | Actress who was the first female host of "Saturday Night Live": 2 wds. |
| 43% | NANCYPELOSI | 11 | Democratic congresswoman from California who was the first female Speaker of the House: 2 wds. |
| 43% | AMELIAEARHART | 13 | Aviation pioneer who was the first woman to fly solo across the Atlantic: 2 wds. |
| 43% | CANDICEBERGEN | 13 | "Murphy Brown" star who was the first female host of "Saturday Night Live": 2 wds. |
| 43% | SHERYLSWOOPES | 13 | Openly gay basketballer who was the first woman to be signed by the WNBA: 2 wds. |
| 43% | NAOMICAMPBELL | 13 | British supermodel who was the first Black model on the cover of Vogue France: 2 wds. |
| 43% | TENZINGYATSO | 12 | 14th Dalai Lama who was the first Tibetan to win the Nobel Peace Prize: 2 wds. |
| 43% | WALTERJOHNSON | 13 | Senators pitcher who was inducted in the first Hall of Fame ceremony: 2 wds. |
| 42% | YURIGAGARIN | 11 | Russian who was the first person to travel into space and orbit the earth (1961): 2 wds. |
| 42% | HALLEBERRY | 10 | "Swordfish" actress who was the first runner-up in the Miss USA pageant in 1986: 2 wds. |
| 42% | MUHAMMADYUNUS | 13 | Social entrepreneur and economist who was the first Bangladeshi to win the Nobel Peace Prize: 2 wds. |
| 42% | WARRENMOON | 10 | Undrafted quarterback who was the first African American quarterback inducted into the Hall of Fame: 2 wds. |
| 42% | MOMSMABLEY | 10 | Trailblazing African American who was the first female comedian to perform at the Apollo Theater: 2 wds. |
| 42% | SHERYLSWOOPES | 13 | Basketball Hall of Fame inductee who was the first player to sign with the WNBA: 2 wds. |
| 42% | NATEROBINSON | 12 | NBA point guard listed at 5'9" who was the first three-time slam dunk champion: 2 wds. |
| 42% | LISALESLIE | 10 | Basketball Hall of Fame inductee who was the first player to dunk in a WNBA game: 2 wds. |
| 42% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who was the Bee on season 1 of "The Masked Singer": 2 wds. |
| 42% | NAOMICAMPBELL | 13 | "American Horror Story: Hotel" actress who was the first black model on the cover of French Vogue : 2 wds. |
| 42% | ANNPRESTON | 10 | American physician and activist who was the first female dean of a medical school in the world: 2 wds. |
| 42% | SEATTLESLEW | 11 | 1977 Triple Crown winner who was the first American champion to have been undefeated in previous races: 2 wds. |
| 42% | JOANRIVERS | 10 | Comedian who was the first woman to host a late-night talk show on a major network: 2 wds. |