| 100% | MILKCAN | 7 | Trophy given to the winner of the Fresno State vs. Boise State football game: 2 wds. |
| 45% | STANLEYCUP | 10 | Trophy awarded to the winners of the NHL championship (2 wds.) |
| 39% | PAULBUNYANAXE | 13 | Prize awarded to the winner of the Minnesota-Wisconsin football game, colloquially, with "the" |
| 38% | SIDNEYCROSBY | 12 | Penguins center and third back-to-back winner of the Conn Smythe Trophy (2016-2017): 2 wds. |
| 38% | MARIOLEMIEUX | 12 | Penguins center and second back-to-back winner of the Conn Smythe Trophy (1991-1992): 2 wds. |
| 38% | BERNIEPARENT | 12 | Flyers goalie and first back-to-back winner of the Conn Smythe Trophy (1974-1975): 2 wds. |
| 38% | WOODROWWILSON | 13 | 28th President of the United States from 1913 to 1921: 2 wds. |
| 37% | AXE | 3 | Stanford ___ (head of a weapon used as a trophy for the winner of the annual Stanford-Cal football game) |
| 37% | AMORE | 5 | "We the people of the United States, in order to form ___ perfect union ...": 2 wds. |
| 35% | CRYSTALBALL | 11 | Nickname of the championship trophy awarded to 18-Across: 2 wds. |
| 35% | IRONHORSE | 9 | The ___, nickname given to baseballer Lou Gehrig of the New York Yankees: 2 wds. |
| 35% | HAILMARY | 8 | Long, desperate pass at the end of a football game: 2 wds. |
| 35% | ROSES | 5 | Flowers in a wreath given to the winner of the Kentucky Derby |
| 35% | NEWYORK | 7 | State that's home to Lake Placid, site of the 1980 Winter Olympics: 2 wds. |
| 35% | CHRISHARRISON | 13 | Host of the game show "Who Wants to Be a Millionaire": 2 wds. |
| 34% | FOLLOWSUIT | 10 | Term originating through card games that means to copy the actions of the one before you: 2 wds. |
| 34% | MARCUSMARIOTA | 13 | 2014 Heisman Trophy winner who led his team to the Pac-12 title: 2 wds. |
| 34% | COMMISSIONERS | 13 | ___ Trophy, prize presented to the winner of the annual MLB World Series |
| 34% | LISALESLIE | 10 | Basketball Hall of Fame inductee who was the first player to dunk in a WNBA game: 2 wds. |
| 33% | AUDREYHEPBURN | 13 | Only EGOT winner to earn two of the awards posthumously (2 wds.) |
| 33% | HIDDENFIGURES | 13 | Name given to the team of NASA mathematicians who performed calculations for early space launches (2 wds.) |
| 33% | RACHELCARSON | 12 | 19-Across and 34-Across writer whose work indirectly led to the creation of the United States Environmental Protection Agency (2 wds.) |
| 33% | UPTOWNFUNK | 10 | 2014 Mark Ronson hit that later had to give members of the Gap Band songwriting credits: 2 wds. |
| 33% | NANCYREAGAN | 11 | First Lady of the United States (1981-1989) who wrote "To Love a Child": 2 wds. |
| 33% | RAINMAN | 7 | Winner of the Academy Award for Best Picture of 1988: 2 wds. |
| 33% | BALDEAGLE | 9 | Bird on the seal of the United States: 2 wds. |
| 33% | EDDIEGEORGE | 11 | Heisman Trophy winner and college football coach who appeared in a Broadway production of "Chicago" in 2016: 2 wds. |
| 33% | TAKUMASATO | 10 | Winner of the 2017 Indianapolis 500: 2 wds |
| 32% | MICHELLEOBAMA | 13 | First African-American woman to serve as First Lady of the United States (2 wds.) |
| 32% | JOHNMADDEN | 10 | Football player turned broadcaster who was the first one to have worked for all of the "Big Four" TV networks: 2 wds. |