| 100% | MARIOLEMIEUX | 12 | Penguins center and second back-to-back winner of the Conn Smythe Trophy (1991-1992): 2 wds. |
| 84% | SIDNEYCROSBY | 12 | Penguins center and third back-to-back winner of the Conn Smythe Trophy (2016-2017): 2 wds. |
| 68% | BERNIEPARENT | 12 | Flyers goalie and first back-to-back winner of the Conn Smythe Trophy (1974-1975): 2 wds. |
| 58% | MARIOLEMIEUX | 12 | Second player to win the NHL's Conn Smythe Trophy in consecutive years (1991, 1992) (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. |
| 42% | MILKCAN | 7 | Trophy given to the winner of the Fresno State vs. Boise State football game: 2 wds. |
| 42% | PATRICKROY | 10 | Montreal Canadiens and Colorado Avalanche goalie who won the Conn Smythe Trophy in 1986, 1993, and 2001: 2 wds. |
| 41% | JAREDLETO | 9 | "House of Gucci" actor and lead singer of the band Thirty Seconds to Mars: 2 wds. |
| 41% | STANLEYCUP | 10 | Trophy awarded to the winners of the NHL championship (2 wds.) |
| 40% | RODCAREW | 8 | Minnesota Twins first and second baseman who was inducted into the Baseball Hall of Fame in 1991: 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. |
| 40% | SIDNEY | 6 | With 32-Across, Penguins center who won the Conn Smythe Trophy as MVP of the NHL playoffs |
| 39% | RONHEXTALL | 10 | Philadelphia Flyers goalie who won the Conn Smythe Trophy in 1987: 2 wds. |
| 39% | DAVIDROBINSON | 13 | Hall of Fame Spurs center who played on both the 1992 and 1996 US "Dream Team": 2 wds. |
| 39% | RYANOREILLY | 11 | 2019 Conn Smythe Trophy winner who led the 44-Across in scoring (2 wds.) |
| 39% | JONATHANQUICK | 13 | Los Angeles Kings goalie who won the Conn Smythe Trophy in 2012: 2 wds. |
| 39% | SIDNEYCROSBY | 12 | Third player to win the NHL's Conn Smythe Trophy in consecutive years (2016, 2017) (2 wds.) |
| 39% | BERNIEPARENT | 12 | First player to win the NHL's Conn Smythe Trophy in consecutive years (1974, 1975) (2 wds.) |
| 39% | ESSEX | 5 | Cricket team; winners of the County Championship in 1991 and 1992 |
| 38% | STEPHENIEMEYER | 14 | "Twilight" author and winner of a National Merit Scholarship in 1992: 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% | MAEJEMISON | 10 | The first Black female astronaut and winner of a National Achievement Scholarship in 1973: 2 wds. |
| 36% | RUDYGOBERT | 10 | Jazz center who won his second consecutive Defensive Player of the Year Award in 2019: 2 wds. |
| 36% | CRYSTALBALL | 11 | Nickname of the championship trophy awarded to 18-Across: 2 wds. |
| 35% | LOUISARMSTRONG | 14 | Jazz legend and onetime neighbor of the USTA National Tennis Center, for whom its second-largest stadium is named (2 wds.) |
| 35% | MARIOLEMIEUX | 12 | Penguins center who was the third player to have a 100-assist season: 2 wds. |
| 35% | BRUNOMARS | 9 | Winner of Album, Record, and Song of the Year at the 2018 Grammys: 2 wds. |
| 35% | ALLISONJANNEY | 13 | 2014 and 2015 winner of the Emmy for Outstanding Supporting Actress in a Comedy for "Mom": 2 wds. |
| 34% | CONNORMCDAVID | 13 | Edmonton Oilers captain who was honored with the NHL's Conn Smythe Trophy in 2024 (2 wds.) |