| 100% | PULITZERPRIZE | 13 | Award won by 40-Across for 18-Across (2 wds.) |
| 80% | PULITZERPRIZE | 13 | Award won by 18-Across for "Beloved" (2 wds.) |
| 73% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 70% | PULITZERPRIZE | 13 | Award won by 18-Across (2 wds.) |
| 68% | PULITZERPRIZE | 13 | Prestigious award for authors, won by 42-Across for her first novel: 2 wds. |
| 67% | VIDEOVANGUARD | 13 | Achievement award won by 17-Across in 1987 (it was renamed in 1991 for Michael Jackson): 2 wds. |
| 67% | NOBELPRIZE | 10 | Award 18-Across won twice, for her work in physics and chemistry: 2 wds. |
| 66% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 65% | RULEOFWOLVES | 12 | Novel by 40-Across that won the 2021 Goodreads Choice Award for Young Adult Fantasy (3 wds.) |
| 65% | THEBANDSVISIT | 13 | Broadway show by 40-Across starring 18-Across and Tony Shalhoub that won 10 2018 Tony Awards, including Best Musical (3 wds.) |
| 63% | BESTFOLKALBUM | 13 | 2012 Grammy won by 44-Across for 18-Across: 3 wds. |
| 63% | BESTACTRESS | 11 | Oscar that 32-Across won for 18-Across: 2 wds. |
| 63% | EMMYAWARD | 9 | Honor won twice by 18-Across in the 1950s for playing Schultzy on "The Bob Cummings Show": 2 wds. |
| 61% | FLOOREXERCISE | 13 | Gymnastics event won by 40-Across at the 18-Across and five times at the World Championships (2 wds.) |
| 61% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 60% | NCAAWOMENS | 10 | With 40-Across, sport whose annual tournament was won this past Tuesday by the University of Connecticut, for the tenth time: 2 wds. |
| 60% | SHELLGAME | 9 | 2018 novel by 40-Across featuring 18-Across (2 wds.) |
| 59% | MAKINGIT | 8 | Reality TV competition for craftspeople, cohosted by 18-Across: 2 wds. |
| 59% | THEFRIEND | 9 | Book that won the 2018 National Book Award for Fiction, written by Sigrid Nunez: 2 wds. |
| 59% | SILVERSLUGGER | 13 | NL batting award won by 14-Across in 2000, 2002, and 2003: 2 wds. |
| 59% | BESTACTOR | 9 | Oscar won by 21-Across for "The King's Speech": 2 wds. |
| 59% | WONDERWOMAN | 11 | Superhero film by Patty Jenkins that won the 2018 Hugo Award for Best Dramatic Presentation: 2 wds. |
| 59% | THEAVENGERS | 11 | Superhero film by Joss Whedon that won the 2013 Hugo Award for Best Dramatic Presentation: 2 wds. |
| 58% | MELISSALEO | 10 | She won the Oscar and Golden Globe for Best Supporting Actress for 18-Across: 2 wds. |
| 58% | CHRISTIANBALE | 13 | He won the Oscar and Golden Globe for Best Supporting Actor for 18-Across: 2 wds. |
| 58% | ARCHIEMANNING | 13 | College Football Hall of Famer whose sons Peyton and Eli both won the NFL Man of the Year award named for 18-Across (2 wds.) |
| 58% | LEIGHBARDUGO | 12 | 18-Across and 29-Across writer whose novel "Ninth House" won the 2019 Goodreads Choice Award for Best Fantasy (2 wds.) |
| 57% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 57% | BATTINGTITLES | 13 | 18-Across and 40-Across have each won these in both major leagues: 2 wds. |
| 57% | PEOPLESCHOICE | 13 | Award 18-Across won in January 2016 as Favorite Breakout Artist: 2 wds. |