| 100% | PEOPLESCHOICE | 13 | Award 18-Across won in January 2016 as Favorite Breakout Artist: 2 wds. |
| 46% | NOBELPRIZE | 10 | Award 18-Across won twice, for her work in physics and chemistry: 2 wds. |
| 35% | MEGHANTRAINOR | 13 | 18-Across, 40-Across, and "All About That Bass" singer who has won two "Billboard" Music Awards and a "Billboard" Women in Music Chart-Topper Award (2 wds.) |
| 34% | PULITZERPRIZE | 13 | Award won by 18-Across (2 wds.) |
| 33% | RIOOLYMPICS | 11 | International competition where 40-Across won four gold medals in 2016 (2 wds.) |
| 33% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 33% | PULITZERPRIZE | 13 | Award won by 18-Across for "Beloved" (2 wds.) |
| 33% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 32% | TIGERWOODS | 10 | Golfer who won 18-Across in 1997, also as a 21-year-old: 2 wds. |
| 32% | THEOPEN | 7 | Major golf tournament that 30-Across won in Scotland in 2013: 2 wds. |
| 32% | PULITZERPRIZE | 13 | Award won by 40-Across for 18-Across (2 wds.) |
| 32% | PULITZERPRIZE | 13 | Prestigious award won in 2018 by "DAMN.": 2 wds. |
| 31% | MYCOUSINVINNY | 13 | 1992 courtroom comedy for which 18-Across won an Academy Award: 3 wds. |
| 31% | ACA | 3 | Award, now discontinued, that Brad Paisley won as Male Artist of the Year in 2010 and 2011 (abbr.) |
| 31% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 30% | TONYAWARD | 9 | Honor that 33-/35-Across won in ten categories, including Best Musical: 2 wds. |
| 30% | JULIANFELLOWES | 14 | 18-Across and 44-Across writer/creator who won an Academy Award for Best Original Screenplay for "Gosford Park" (2 wds.) |
| 30% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 30% | LEIGHBARDUGO | 12 | 18-Across and 29-Across writer whose novel "Ninth House" won the 2019 Goodreads Choice Award for Best Fantasy (2 wds.) |
| 30% | SARABAREILLES | 13 | "Love Song" singer/pianist who performed a duet with 18-Across at the Grammy Awards in 2014 (2 wds.) |
| 30% | ASBRAVEASYOU | 12 | 29-Across novel that won the Kirkus Prize in 2016 and the NAACP Image Award for Outstanding Literary Work for Youth/Teen in 2017 (4 wds.) |
| 30% | THENOTEBOOK | 11 | 2004 romantic drama starring 18-Across and 32-Across that was adapted as a Broadway musical in 2024 (2 wds.) |
| 30% | EMILYHENRY | 10 | 18-Across, 26-Across, and 35-Across novelist who won the 2021, 2022, and 2023 Goodreads Choice Award for Best Romance (2 wds.) |
| 29% | DAVIDCHANG | 10 | Five-time 18-Across Award-winning restaurateur who founded Momofuku (2 wds.) |
| 29% | SPINGARNMEDAL | 13 | NAACP award that John Lewis won in 2002: 2 wds. |
| 29% | MIKETROUT | 9 | LA Angel who won the AL MVP award in 2014, 2016, and 2019: 2 wds. |
| 29% | CLINTBLACK | 10 | 18-Across, 26-Across, and 35-Across country singer who won four 1989 Academy of Country Music Awards, including Top Male Vocalist (2 wds.) |
| 29% | IGGYAZALEA | 10 | "Fancy" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist in 2014: 2 wds. |
| 29% | JANEHARPER | 10 | 18-Across and 33-Across writer whose novel "The Dry" won the British Book Award for Crime & Thriller Book of the Year 2018 (2 wds.) |
| 29% | BATTINGTITLES | 13 | 18-Across and 40-Across have each won these in both major leagues: 2 wds. |