| 100% | TWICE | 5 | How many times the Minnesota Twins have won the World Series, appropriately |
| 73% | ONCE | 4 | How many times the Washington Nationals have won the World Series |
| 60% | TWO | 3 | Number of times the Twins have won the World Series, appropriately |
| 49% | YANKEES | 7 | Team that has won the World Series a record 27 times |
| 48% | BRAVES | 6 | Team that has won the World Series three times while based in three different cities |
| 45% | LICEY | 5 | Tigres del ___, Dominican team that has won the Caribbean World Series nine times |
| 44% | YANKEES | 7 | The New York ___, MLB team that has won the most number of World Series championships with 27 wins |
| 41% | 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. |
| 40% | TOM | 3 | ___ Curren, American surfer who has won the world championship three times |
| 40% | ONCE | 4 | How many times Leonardo DiCaprio has won an Oscar? |
| 40% | THRICE | 6 | How many times London has hosted the Summer Olympics |
| 39% | AUSTRALIA | 9 | Country that has won the most Cricket World Cups |
| 39% | NEVER | 5 | How many times a one-point safety has occurred in the NFL |
| 37% | TAIWAN | 6 | Island with the most Little League World Series wins |
| 37% | GERMANY | 7 | Country home to Franz Beckenbauer, that has won the FIFA World Cup 4 times |
| 37% | BRAZIL | 6 | Country home to Pele, that has won the FIFA World Cup a record 5 times |
| 36% | MARINERS | 8 | Seattle team that did not win the World Series despite tying the regular season record for most wins in 2001 |
| 36% | PADRES | 6 | One of five MLB teams that has appeared in the World Series but never won the title |
| 35% | MACAU | 5 | The gambling capital of the world which has almost 24 times more tourists than local residents |
| 35% | PEYTONMANNING | 13 | Former NFL quarterback who has won the AP NFL Most Valuable Player Award five times (highest in history): Abbr. |
| 35% | SWEPT | 5 | Won the World Series in four games, say |
| 35% | SWEEP | 5 | Win the World Series in four games, say |
| 34% | MMII | 4 | Year the Angels won the World Series |
| 34% | AWAY | 4 | Like the winning team in every World Series game, for the first time ever (October, 2019) |
| 34% | MIKAELA | 7 | "Talk snow sports, talk of ___ Shiffrin," alpine skier and two-time Olympic Gold medalist who has the most World Cup wins |
| 34% | PIRATES | 7 | Team that last won the World Series in 1979 |
| 33% | FOUROUT | 7 | With 38-Across, games required to win the World Series |
| 33% | SLATER | 6 | Kelly ___, American surfer who has won the World Surf League |
| 33% | TWICE | 5 | How many times Bette Davis won Best Actress |
| 33% | TEN | 3 | How many amendments the Bill of Rights has |