| 100% | MANNYFRANCO | 11 | Jockey who won the 31-Across in 2020 riding Tiz the Law (2 wds.) |
| 59% | JOHNVELAZQUEZ | 13 | Jockey who won the Kentucky Derby in 2011, 2017, and 2020 (2 wds.) |
| 57% | JOELROSARIO | 11 | Jockey who won 31-Across in 2019 riding Sir Winston and in 2014 riding Tonalist (2 wds.) |
| 55% | SOFIAKENIN | 10 | American tennis player who won the Australian Open in 2020: 2 wds. |
| 52% | KIMALIM | 7 | South Korean golfer who won the women's 35-Across in 2020 (2 wds.) |
| 52% | JOHNVELAZQUEZ | 13 | Jockey who won the Kentucky Derby in 2011 and 2017 (2 wds.) |
| 52% | RODDYRICCH | 10 | "The Box" rapper who won the BET Award for Best New Artist in 2020: 2 wds. |
| 51% | LOUISEGLUCK | 11 | "The Wild Iris" poet from the US who won the Nobel Prize in Literature in 2020: 2 wds. |
| 51% | GARTHBROOKS | 11 | "Friends in Low Places" singer who won the 2020 Gershwin Prize: 2 wds. |
| 50% | MIGUELCABRERA | 13 | Slugger who won the 34-Across in 2012: 2 wds. |
| 49% | DEVINWILLIAMS | 13 | Brewers pitcher who the won National League Rookie of the Year Award in 2020: 2 wds. |
| 49% | MARLONBRANDO | 12 | Two-time Oscar winner who portrayed the rogue colonel in 31-Across: 2 wds |
| 49% | JOSEABREU | 9 | First baseman for the White Sox who won the American League MVP award in 2020: 2 wds. |
| 49% | JEREMYSTRONG | 12 | "Succession" star who won the 2020 Emmy for Outstanding Lead Actor in a Drama Series: 2 wds. |
| 49% | JADECAREY | 9 | US gymnast who won gold in women's floor exercise at the 2020 Tokyo Olympics: 2 wds. |
| 49% | DAWNSTALEY | 10 | Basketball Hall of Fame inductee who won four Coach of the Year awards in 2020: 2 wds. |
| 48% | TEDDYROOSEVELT | 14 | Mascot in jersey #26 who has the least overall wins (138 as of 2020) of the four main 16-Across competitors: 2 wds. |
| 48% | ABRAHAMLINCOLN | 14 | Mascot in jersey #16 who has the most overall wins (371 as of 2020) of the four main 16-Across competitors: 2 wds. |
| 48% | SOFIAKENIN | 10 | American tennis player who won the Women's Tennis Association's Player of the Year in 2020: 2 wds. |
| 48% | REGINAKING | 10 | "Watchmen" star who won the 2020 Emmy for Outstanding Lead Actress in a Limited Series or Movie: 2 wds. |
| 48% | EUGENELEVY | 10 | "Schitt's Creek" star who won the 2020 Emmy for Outstanding Lead Actor in a Comedy Series: 2 wds. |
| 48% | IGASWIATEK | 10 | Polish 33-Across player who won the women's singles championship at Roland-Garros in 2020 and 2022 (2 wds.) |
| 48% | MYKAYLASKINNER | 14 | US gymnast who won silver in women's vault at the 2020 Tokyo Olympics: 2 wds. |
| 47% | LOUISEGLUCK | 11 | American poet who won the 2020 Nobel Prize in Literature (2 wds.) |
| 47% | LOUISEGLUCK | 11 | American writer who won the 2020 Nobel Prize in Literature (2 wds.) |
| 47% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 47% | IGASWIATEK | 10 | Polish tennis player who won the women's singles championship at the 44-Across in 2020, 2022, 2023, and 2024 (2 wds.) |
| 47% | SUNISALEE | 9 | US gymnast who won gold in women's individual all-around at the 2020 Tokyo Olympics: 2 wds. |
| 46% | GEORGSOLTI | 10 | Hungarian-British artist who holds the record for the most Grammy Awards won in a lifetime, with 31: 2 wds. |
| 46% | TREVORBAUER | 11 | Cincinnati Reds starting pitcher who led the National League in ERA and won the 2020 Cy Young Award (2 wds.) |