| 100% | BERNIEPARENT | 12 | Flyers goalie and first back-to-back winner of the Conn Smythe Trophy (1974-1975): 2 wds. |
| 68% | SIDNEYCROSBY | 12 | Penguins center and third back-to-back winner of the Conn Smythe Trophy (2016-2017): 2 wds. |
| 68% | MARIOLEMIEUX | 12 | Penguins center and second back-to-back winner of the Conn Smythe Trophy (1991-1992): 2 wds. |
| 58% | BERNIEPARENT | 12 | First player to win the NHL's Conn Smythe Trophy in consecutive years (1974, 1975) (2 wds.) |
| 48% | PATRICKROY | 10 | Montreal Canadiens and Colorado Avalanche goalie who won the Conn Smythe Trophy in 1986, 1993, and 2001: 2 wds. |
| 47% | PATRICKROY | 10 | Former Montreal Canadiens goaltender who has 551 wins and is the only player in NHL history to win the Conn Smythe trophy thrice: 2 wds. |
| 47% | RONHEXTALL | 10 | Philadelphia Flyers goalie who won the Conn Smythe Trophy in 1987: 2 wds. |
| 45% | JONATHANQUICK | 13 | Los Angeles Kings goalie who won the Conn Smythe Trophy in 2012: 2 wds. |
| 42% | MILKCAN | 7 | Trophy given to the winner of the Fresno State vs. Boise State football game: 2 wds. |
| 42% | MAEJEMISON | 10 | The first Black female astronaut and winner of a National Achievement Scholarship in 1973: 2 wds. |
| 41% | ARCHIEGRIFFIN | 13 | Only player to win the 15-Across twice, in 1974 and 1975: 2 wds. |
| 41% | CHRISEVERT | 10 | Tennis player who won the AP Athlete of the Year award in 1974, 1975, 1977, and 1980: 2 wds. |
| 41% | STANLEYCUP | 10 | Trophy awarded to the winners of the NHL championship (2 wds.) |
| 40% | MARCUSALLEN | 11 | Hall of Fame Raiders/Chiefs running back who won the 1981 Heisman Trophy and the 1984 Super Bowl: 2 wds. |
| 40% | TONYDORSETT | 11 | Hall of Fame Cowboys/Broncos running back who won the 1976 Heisman Trophy and the 1978 Super Bowl: 2 wds. |
| 39% | RYANOREILLY | 11 | 2019 Conn Smythe Trophy winner who led the 44-Across in scoring (2 wds.) |
| 39% | SIDNEYCROSBY | 12 | Third player to win the NHL's Conn Smythe Trophy in consecutive years (2016, 2017) (2 wds.) |
| 39% | MARIOLEMIEUX | 12 | Second player to win the NHL's Conn Smythe Trophy in consecutive years (1991, 1992) (2 wds.) |
| 38% | MARCOPOLO | 9 | Venetian explorer, who is known to be the first to have detailed accounts of travel to, and about China: 2 wds. |
| 38% | JOHNOHURLEY | 11 | "Family Feud" host from 2006 to 2010, and runner-up on the first season of "Dancing With the Stars": 2 wds. |
| 38% | BUZZALDRIN | 10 | Lunar module pilot on the Apollo 11 mission and one of the first two humans to land on the moon: 2 wds. |
| 38% | ASHLEIGHBARTY | 13 | Winner of the 2022 Australian Open, the first Australian woman to win a singles title there since 1978 (2 wds.) |
| 37% | MARTHAGRAHAM | 12 | American dancer who was the first dancer to perform at the White House and to receive the Presidential Medal of Freedom: 2 wds. |
| 37% | STEVIENICKS | 11 | American singer and songwriter who became the first woman to be inducted twice into the Rock and Roll Hall of Fame: 2 wds. |
| 37% | EDMUNDHILLARY | 13 | Mountaineer who climbed Mount Everest with Tenzing Norgay and became the first climbers to have reached the summit of the mountain: 2 wds. |
| 37% | JUNECARTERCASH | 14 | "Ring of Fire" songwriter and five-time Grammy winner whose first name is a month of the year (2 wds.) |
| 37% | HANKAARON | 9 | Braves and Brewers star who gained first-ballot induction to the Baseball Hall of Fame in 1982 with 97.8% of the vote: 2 wds. |
| 36% | TIGERWOODS | 10 | First winner of the PGA's FedEx Cup (2007) (2 wds.) |
| 36% | EVELYNASHFORD | 13 | The first track and field athlete to run 100 meters under 11 seconds in an Olympic Games and who has won a total of 5 Olympic medals: 2 wds. |
| 36% | STEPHENSTILLS | 13 | American singer and songwriter who is the first artist to be inducted twice on the same night into the Rock and Roll Hall of Fame: 2 wds. |