| 100% | JOEMAZZULLA | 11 | 28-Across head coach who is the youngest to win the NBA Finals since Bill Russell in 1969 (2 wds.) |
| 44% | SEANMCVAY | 9 | 2017 AP NFL Coach of the Year who is the youngest head coach to win the Super Bowl (with the 2022 21-Across Rams) (2 wds.) |
| 40% | PAULMAURICE | 11 | Florida Panthers head coach who led the team to the Stanley Cup Final in both of his first two seasons (2 wds.) |
| 40% | LARRYNANCE | 10 | Phoenix Suns player who was the first player to ever win the NBA Slam Dunk Contest in 1984: 2 wds. |
| 39% | KIMMULKEY | 9 | Coach of 41-Across who is the only coach in women's college basketball to win national championships with two teams (2 wds.) |
| 39% | KIMMULKEY | 9 | Coach of the 40-Across who is the only coach in women's college basketball to win national championships with two teams (2 wds.) |
| 38% | BILLRUSSELL | 11 | 2021 Basketball Hall of Fame inductee who was the first Black head coach in the NBA (2 wds.) |
| 38% | LEANNRIMES | 10 | Singer who is the youngest ever individual artist to win the Grammy: 2 wds. |
| 37% | NICKSIRIANNI | 12 | Eagles head coach who led his team to victory in the 2025 Super Bowl: 2 wds. |
| 37% | GWENJORGENSEN | 13 | American distance runner and two-time ITU World Champion who was the first to win a triathlon gold for USA in the Olympics: 2 wds. |
| 37% | DANIILMEDVEDEV | 14 | Russian tennis pro whose 2024 loss to 28-Across was his third appearance in the Australian Open finals without a win (2 wds.) |
| 37% | RORYMCILROY | 11 | Northern Irish pro golfer and four-time major champion who was the youngest to earn 10 million euros in career earnings: 2 wds. |
| 36% | BILLRUSSELL | 11 | Hall-of-Fame Celtics center whose name was added to the NBA Finals MVP Award in 2009: 2 wds. |
| 36% | MARGARETCOURT | 13 | Australian tennis player who was the first woman to win the Grand Slam in the Open Era: 2 wds. |
| 36% | TONYDUNGY | 9 | Hall-of-Famer who was the first Black head coach to win a 15 Across |
| 36% | TYRONNLUE | 9 | NBA coach for the Cavaliers who won the championship in 2016: 2 wds. |
| 36% | PETESAMPRAS | 11 | Youngest man in tennis's Open Era to win the US Open, at 19 years, 28 days (1990): 2 wds. |
| 36% | PETESAMPRAS | 11 | Tennis great who is the youngest player to win the US Open Men's Singles championship (2 wds.) |
| 36% | JAYLENBROWN | 11 | 28-Across guard who was named Most Valuable Player of the 2024 NBA Finals (2 wds.) |
| 36% | JASONKIDD | 9 | Former NBA guard who will coach the Bucks in 2014: 2 wds. |
| 36% | DEREKFISHER | 11 | Former NBA guard who will coach the Knicks in 2014: 2 wds. |
| 36% | STEVEKERR | 9 | Former NBA guard who will coach the Warriors in 2014: 2 wds. |
| 36% | JIMMYBUTLER | 11 | NBA All-Star who was traded to the Timberwolves in 2017 after six years with the Bulls: 2 wds. |
| 36% | STEVEKERR | 9 | NBA coach for the Warriors who won the championship in 2015 and 2017: 2 wds. |
| 36% | MARKDAIGNEAULT | 14 | Oklahoma City Thunder head coach who was voted NBA Coach of the Year for the 2023-24 season (2 wds.) |
| 36% | CHUCKDALY | 9 | Two-time NBA championship-winning head coach who won Olympic gold with Team USA in 1992: 2 wds. |
| 36% | GREGGPOPOVICH | 13 | Five-time NBA championship-winning head coach who won Olympic gold with Team USA in 2021: 2 wds. |
| 36% | STEVEKERR | 9 | Four-time NBA championship-winning head coach who won Olympic gold with Team USA in 2024: 2 wds. |
| 36% | MIKEDANTONI | 11 | L.A. Lakers head coach who succeeded the interim coach who followed 27-Across in 2012: 2 wds. |
| 36% | LLEYTONHEWITT | 13 | Australian tennis player who, at 20, was the youngest man to be ranked #1 in singles: 2 wds. |