| 100% | BILLHARTACK | 11 | One of two jockeys who won the Kentucky Derby five times (2 wds.) |
| 100% | EDDIEARCARO | 11 | One of two jockeys who won the Kentucky Derby five times (2 wds.) |
| 57% | JOHNVELAZQUEZ | 13 | Jockey who won the Kentucky Derby in 2011, 2017, and 2020 (2 wds.) |
| 56% | JOHNVELAZQUEZ | 13 | Jockey who won the Kentucky Derby in 2011 and 2017 (2 wds.) |
| 49% | BJORNBORG | 9 | One of only two players in the modern era to win five straight 17-Across Gentlemen's Singles Finals (1976-1980): 2 wds. |
| 49% | ROGERFEDERER | 12 | One of only two players in the modern era to win five straight 17-Across Gentlemen's Singles Finals (2003-2007): 2 wds. |
| 48% | MICHAELCOOPER | 13 | One of the greatest players of the LA Lakers who won five NBA Championships and eight All-Defensive Teams with the team: 2 wds. |
| 48% | HELENHAYES | 10 | Actress who won the Emmy, Grammy, Oscar, and Tony (one of her two Oscars was for "Airport"): 2 wds. |
| 48% | BYRONSCOTT | 10 | One of the greatest players of the LA Lakers who won three NBA Championships and went on to coach the team for two years: 2 wds. |
| 46% | FRANKSINATRA | 12 | One of two singers to win 33-Across three times as a solo artist: 2 wds. |
| 46% | STEVIEWONDER | 12 | One of two singers to win 33-Across three times as a solo artist: 2 wds. |
| 45% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 45% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 44% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 44% | PETEALONSO | 10 | N.Y. Mets rookie first baseman who won the 2019 Home Run Derby and drove in two of the National League's runs in the 2019 13-Across (2 wds.) |
| 43% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 43% | SMOKEYROBINSON | 14 | "I Second That Emotion" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 43% | WILLIENELSON | 12 | "Always on My Mind" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 43% | TIGERWOODS | 10 | Golfer who has won the Masters Tournament five times (2 wds.) |
| 43% | SIMONEBILES | 11 | Gymnast of Nike commercials who won five medals at the 2016 Olympic Games: 2 wds. |
| 42% | ARTHURASHKIN | 12 | American scientist who won one half of the 2018 Nobel Prize in Physics for his work on optical tweezers: 2 wds. |
| 42% | DEREKBELL | 9 | Former racing driver from Britain who has won the 24 Hours of Le Mans five times: 2 wds. |
| 42% | MISSYFRANKLIN | 13 | Five-time Olympic swimming gold medalist who won Female Athlete of the Year at the 2011 and 2012 Golden Goggle Awards: 2 wds. |
| 41% | GREGGPOPOVICH | 13 | NBA coach for the Spurs who won the championship five times, including 2014: 2 wds. |
| 41% | JIMTHORPE | 9 | NFL player who won two gold medals in the 1912 Olympics, and a charter member of the Pro Football Hall of Fame: 2 wds. |
| 41% | TENZINGNORGAY | 13 | Sherpa who was one of the first two people to conquer Mount Everest: 2 wds. |
| 41% | TRIPLECROWN | 11 | Distinction of winning the Kentucky Derby, the Preakness, and the Belmont Stakes in the same year (2 wds.) |
| 40% | KELLYCLARKSON | 13 | Female singer who won the inaugural season of "American Idol": 2 wds. |
| 40% | ATOE | 4 | One of the five digits on your foot: 2 wds. |
| 40% | PAULMCCARTNEY | 13 | One of the two singers on 15-Across: 2 wds. |