| 100% | MARIOLEMIEUX | 12 | Second player to win the NHL's Conn Smythe Trophy in consecutive years (1991, 1992) (2 wds.) |
| 81% | SIDNEYCROSBY | 12 | Third player to win the NHL's Conn Smythe Trophy in consecutive years (2016, 2017) (2 wds.) |
| 81% | BERNIEPARENT | 12 | First player to win the NHL's Conn Smythe Trophy in consecutive years (1974, 1975) (2 wds.) |
| 45% | 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. |
| 45% | CONNORMCDAVID | 13 | Edmonton Oilers captain who was honored with the NHL's Conn Smythe Trophy in 2024 (2 wds.) |
| 41% | CONNORMCDAVID | 13 | Oilers captain who is the most recent NHL player to win the Art Ross Trophy (for most points in the regular season) twice: 2 wds. |
| 40% | RONHEXTALL | 10 | Philadelphia Flyers goalie who won the Conn Smythe Trophy in 1987: 2 wds. |
| 39% | JONATHANQUICK | 13 | Los Angeles Kings goalie who won the Conn Smythe Trophy in 2012: 2 wds. |
| 39% | ARCHIEGRIFFIN | 13 | Only player to win the 15-Across twice, in 1974 and 1975: 2 wds. |
| 38% | NATEROBINSON | 12 | Only player to win the NBA Slam Dunk Contest three times, in 2006, 2009, and 2010: 2 wds. |
| 38% | DWIGHTHOWARD | 12 | Tallest player to win the NBA Slam Dunk Contest, in 2008: 2 wds. |
| 37% | LLEYTONHEWITT | 13 | Second-youngest man in tennis's Open Era to win the US Open, at 20 years, 6 months, 13 days (2001): 2 wds. |
| 37% | SOFIAKENIN | 10 | American tennis player who won the Women's Tennis Association's Player of the Year in 2020: 2 wds. |
| 37% | MARIOLEMIEUX | 12 | Penguins center and second back-to-back winner of the Conn Smythe Trophy (1991-1992): 2 wds. |
| 37% | PATRICKROY | 10 | Montreal Canadiens and Colorado Avalanche goalie who won the Conn Smythe Trophy in 1986, 1993, and 2001: 2 wds. |
| 36% | PRINCEFIELDER | 13 | Rangers designated hitter who won the MLB Comeback Player of the Year Award in 2015: 2 wds. |
| 36% | MARIANORIVERA | 13 | Yankees relief pitcher who won the MLB Comeback Player of the Year Award in 2013: 2 wds. |
| 36% | STEFFIGRAF | 10 | Tennis player who is the only player (man or woman) to win a Grand Slam and Olympic gold medal in one year: 2 wds. |
| 36% | RUDYGOBERT | 10 | Jazz center who won his second consecutive Defensive Player of the Year Award in 2019: 2 wds. |
| 36% | STEFFIGRAF | 10 | Tennis player who won the AP Athlete of the Year award in 1989: 2 wds. |
| 35% | RYANOREILLY | 11 | 2019 Conn Smythe Trophy winner who led the 44-Across in scoring (2 wds.) |
| 35% | NAOMIOSAKA | 10 | Japanese tennis player who won the Laureus Breakthrough of the Year award in 2019: 2 wds. |
| 35% | NOVAKDJOKOVIC | 13 | Serbian tennis player who won the Laureus Sportsman of the Year award in 2019: 2 wds. |
| 34% | KAWHILEONARD | 12 | Clippers small forward who won his second consecutive Defensive Player of the Year Award in 2016: 2 wds. |
| 34% | CHRISEVERT | 10 | Tennis player who won the AP Athlete of the Year award in 1974, 1975, 1977, and 1980: 2 wds. |
| 34% | SERENAWILLIAMS | 14 | Tennis player who won the AP Athlete of the Year award in 2002, 2009, 2013, and 2015: 2 wds. |
| 34% | MAHERSHALAALI | 13 | First black actor to win two Oscars in the same category, and only the second to win two competitive Oscars: 2 wds. |
| 33% | PETESAMPRAS | 11 | Youngest man in tennis's Open Era to win the US Open, at 19 years, 28 days (1990): 2 wds. |
| 33% | VICTORHEDMAN | 12 | Tampa Bay Lightning defenseman who won the Conn Smythe Trophy for Most Valuable Player during the 2020 Stanley Cup playoffs (2 wds.) |
| 33% | JIMMIEJOHNSON | 13 | The only driver in NASCAR history to win five consecutive championships: 2 wds. |