| 100% | TONYLARUSSA | 11 | World Series-winning manager in both the AL (A's, 1989) and NL (Cardinals, 2006 and 2011): 3 wds. |
| 47% | FREDMCGRIFF | 11 | Home run leader in both the AL (Blue Jays, 1989) and NL (Padres, 1992): 2 wds. |
| 43% | NEWYORKMETS | 11 | NL East team that lost 101 games in 1967, then won the World Series two years later: 3 wds. |
| 42% | JENNIFERTILLY | 13 | "Liar Liar" actress who has competed in the World Series Poker several times and even won a WSOP bracelet in 2005: 2 wds. |
| 41% | ZANDERSECHRIST | 14 | 19-Across pitcher who had a 3.12 season ERA and was the winning pitcher of the final game of the 2024 Men's College World Series (2 wds.) |
| 41% | TONYLARUSSA | 11 | Athletics/Cardinals manager who won six pennants and three World Series: 3 wds. |
| 40% | BOSTONREDSOX | 12 | Team that won the 2018 World Series making it their ninth win and the fourth one in the 21st century: 3 wds. |
| 40% | TEXASRANGERS | 12 | AL West team that won the franchise's first-ever World Series in 2023, after 62 years: 2 wds. |
| 40% | FRANKROBINSON | 13 | Most Valuable Player in both the AL (Orioles, 1966) and NL (Reds, 1961): 2 wds. |
| 39% | ORSONSCOTTCARD | 14 | "Ender's Game" author who won a Hugo and a Nebula in the same year, twice: 3 wds. |
| 39% | GARYBURGHOFF | 12 | Actor who played "Radar" O'Reilly in both the movie and TV series "M*A*S*H": 2 wds. |
| 38% | DEIONSANDERS | 12 | Only person to play in both the Super Bowl and the World Series: 2 wds. |
| 38% | DEIONSANDERS | 12 | Only athlete to have played in both the World Series and the Super Bowl: 2 wds. |
| 38% | GHANA | 5 | Country that eliminated the U.S.A. in both the 2006 and 2010 FIFA World Cups |
| 38% | BOSTONREDSOX | 12 | Team with which 30-Across won the World Series in 2004: 3 wds. |
| 38% | JEREMYPENA | 10 | 33-Across shortstop who was named MVP of both the American League Championship Series and the World Series in 2022 (2 wds.) |
| 38% | DUSTYBAKER | 10 | 33-Across World Series-winning manager who also won the 1981 World Series as a player (2 wds.) |
| 37% | CHICAGOCUBS | 11 | NL Central team that lost 101 games in 2012, then won the World Series four years later: 2 wds. |
| 37% | HOUSTONASTROS | 13 | AL West team that lost 111 games in 2013, then won the World Series four years later: 2 wds. |
| 37% | WHITESOX | 8 | Chicago MLB team that won the World Series in 1906, 1917, and 2005 (2 wds.) |
| 37% | THEGOODFIGHT | 12 | CBS All Access series set in the world of a Chicago law firm: 3 wds. |
| 37% | STARTREKPICARD | 14 | CBS All Access series set in the future world of a retired Starfleet admiral: 3 wds. |
| 37% | DAVIDPRICE | 10 | Red Sox pitcher who won two games in the 2018 World Series with a 1.98 ERA (2 wds.) |
| 36% | BOSTONREDSOX | 12 | 15-Across team that traded away 45-Across in 1919 and endured the "Curse of the Bambino" until winning the World Series in 2004 (3 wds.) |
| 36% | KENGRIFFEYJR | 12 | He never made it to the World Series despite playing in 2,671 regular-season games with the Mariners, Reds, and White Sox: 3 wds., abbr. |
| 36% | DEION | 5 | Sanders who's played in both the World Series and the Super Bowl |
| 36% | SANDYKOUFAX | 11 | Left-handed pitcher who won his fourth and final World Series with the Dodgers in 1965: 2 wds. |
| 36% | ARTHURCCLARKE | 13 | "Rendezvous With Rama" author who won a Hugo and a Nebula in the same year, twice: 3 wds. |
| 36% | MOORE | 5 | A's pitcher who played in the '89 and '90 World Series |
| 36% | TANEHISICOATES | 14 | "Between the World and Me" author who won a "genius grant" in 2015: 2 wds. |