| 100% | OBIES | 5 | Off-Broadway theater awards won by Annie Baker and Lin-Manuel Miranda |
| 38% | TICKTICKBOOM | 12 | Off Broadway musical made into a 2021 film directed by Lin-Manuel Miranda |
| 35% | DORSEYPRIZES | 12 | Awards won by brother bandleaders Tommy and Jimmy? |
| 35% | TONYS | 5 | Awards won by the musicals "Hamilton" and "Hadestown" |
| 34% | MVP | 3 | Award won by Breanna Stewart in 2018 and 2023 |
| 34% | HAMILTON | 8 | Grammy-winning hit musical written and composed by Lin-Manuel Miranda |
| 34% | OSCARS | 6 | Awards won by Mahershala Ali for “Moonlight” and “Green Book” |
| 34% | OSCAR | 5 | Award won by 19-Across, 33-Across, and 45-Across |
| 34% | HAMILTON | 8 | Hit Broadway musical by Lin-Manuel Miranda |
| 34% | EDGARS | 6 | Awards won by Stephen King and Agatha Christie |
| 34% | ESPYS | 5 | Awards won by LeBron James and David Beckham |
| 34% | OHENRY | 6 | Award won by Alice Munro and Stephen King |
| 34% | ESPY | 4 | Award won by Simone Biles and Serena Williams |
| 34% | OSCAR | 5 | Award won by Paul Newman and Gary Oldman |
| 34% | OBIES | 5 | Theater awards for Off Broadway productions |
| 33% | OSCAR | 5 | Award won by Frances McDormand in 2021 (and 2018 and 1997) |
| 33% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 33% | RECORDOFTHEYEAR | 15 | Grammy award won by "Hello," "Get Lucky" and "Beat It" |
| 33% | BESTPOPALBUM | 12 | Award won twice by Adele and Kelly Clarkson |
| 32% | THEBANDSVISIT | 13 | Broadway show by 40-Across starring 18-Across and Tony Shalhoub that won 10 2018 Tony Awards, including Best Musical (3 wds.) |
| 32% | ESPY | 4 | Award won by Tom Brady for "Best NFL Player" and "Best Male Athlete" |
| 32% | GLOVE | 5 | Gold ___ (fielding award won by 14-Across in 2002 and 2003) |
| 32% | EMMYS | 5 | Awards won this week by John Mulaney and Bill Hader |
| 31% | SILVERSLUGGER | 13 | NL batting award won by 14-Across in 2000, 2002, and 2003: 2 wds. |
| 31% | BESTKISS | 8 | Award won by Kristen Stewart and Robert Pattinson every year from 2009 to 2012 |
| 31% | EMMY | 4 | Award won multiple times by "Modern Family" and "All in the Family" |
| 31% | NOBEL | 5 | With 6-Across, award won by Einstein, Churchill and Sartre |
| 31% | BESTMUSICAL | 11 | Award won by the starts of 17-, 25-, 39- and 52-Across and 11- and 29-Down |
| 30% | OBIE | 4 | Off-Broadway theater awards |
| 30% | OBIES | 5 | Off-Broadway theater awards |