| 100% | PULITZERPRIZE | 13 | Prestigious award won in 2018 by "DAMN.": 2 wds. |
| 58% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 58% | PULITZERPRIZE | 13 | Prestigious award for authors, won by 42-Across for her first novel: 2 wds. |
| 56% | SILVERSLUGGER | 13 | NL batting award won by 14-Across in 2000, 2002, and 2003: 2 wds. |
| 54% | SILVERSLUGGER | 13 | Hitting award won five times by 15-Across, including in 2013: 2 wds. |
| 54% | VIDEOVANGUARD | 13 | Achievement award won by 17-Across in 1987 (it was renamed in 1991 for Michael Jackson): 2 wds. |
| 51% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 50% | MVP | 3 | Award won by Breanna Stewart in 2018 and 2023 |
| 50% | ALLISONJANNEY | 13 | She won the 2018 SAG Award for Female Actor in a Supporting Role for "I, Tonya": 2 wds. |
| 50% | THEFRIEND | 9 | Book that won the 2018 National Book Award for Fiction, written by Sigrid Nunez: 2 wds. |
| 49% | WORLDSERIESMVP | 14 | Award won by Steve Pearce on October 28, 2018: 3 wds. |
| 49% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 49% | OSCAR | 5 | Award won by Frances McDormand in 2021 (and 2018 and 1997) |
| 49% | RACHELCARSON | 12 | "Silent Spring" writer and namesake of the international environmental award won by 32-Across in 2019 (2 wds.) |
| 47% | THEEMISSARY | 11 | Book that won the 2018 National Book Award for Translated Literature, written by Yoko Tawada and translated by Margaret Mitsutani: 2 wds. |
| 47% | PULITZERPRIZE | 13 | Award won by 18-Across for "Beloved" (2 wds.) |
| 47% | PULITZERPRIZE | 13 | Award won by 18-Across (2 wds.) |
| 46% | ROGERFEDERER | 12 | Swiss man who in 2018 won a Grand Slam tournament at age 36: 2 wds. |
| 46% | GEORGSOLTI | 10 | Hungarian-British artist who holds the record for the most Grammy Awards won in a lifetime, with 31: 2 wds. |
| 45% | PULITZERPRIZE | 13 | Award won by 40-Across for 18-Across (2 wds.) |
| 45% | ANNAMAZZOLA | 11 | Author whose novel "The Unseeing" won the 2018 Edgar Award in the Best Paperback Original category: 2 wds. |
| 45% | PEABODY | 7 | Prestigious award won by 17-Across |
| 45% | GRAMMY | 6 | Award won by "DAMN." in the category of Best Rap Album |
| 44% | SILVERSLUGGER | 13 | Batting award won four times by 17-Across and once by 39-Across: 2 wds. |
| 43% | SILVERMEDAL | 11 | Olympic award won twice by figure skater Elvis Stojko (2 wds.) |
| 43% | JOHNCROWLEY | 11 | Author whose short story "Spring Break" won the 2018 Edgar Award in the Best Short Story category: 2 wds. |
| 43% | JASONREYNOLDS | 13 | Author whose novel "Long Way Down" won the 2018 Edgar Award in the Best Young Adult category: 2 wds. |
| 42% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 42% | OBIE | 4 | Award won by Hamilton in 2015 |
| 42% | PEOPLESCHOICE | 13 | Award 18-Across won in January 2016 as Favorite Breakout Artist: 2 wds. |