| 100% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 59% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 54% | SILVERSLUGGER | 13 | NL batting award won by 14-Across in 2000, 2002, and 2003: 2 wds. |
| 53% | ACADEMYAWARDS | 13 | Golden statuettes won by 15- and 26-/34-Across during a February 22 ceremony: 2 wds. |
| 52% | SILVERSLUGGER | 13 | Hitting award won five times by 15-Across, including in 2013: 2 wds. |
| 48% | OSCAR | 5 | Award won by 19-Across, 33-Across, and 45-Across |
| 48% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 48% | TONYAWARD | 9 | 2005 Broadway honor won by 15-Across: 2 wds. |
| 46% | PULITZERPRIZE | 13 | Award won by 18-Across (2 wds.) |
| 46% | SILVERSLUGGER | 13 | Batting award won four times by 17-Across and once by 39-Across: 2 wds. |
| 45% | BESTMUSICAL | 11 | Award won by the starts of 17-, 25-, 39- and 52-Across and 11- and 29-Down |
| 45% | PULITZERPRIZE | 13 | Award won by 18-Across for "Beloved" (2 wds.) |
| 44% | PULITZERPRIZE | 13 | Award won by 40-Across for 18-Across (2 wds.) |
| 44% | ELCAPITAN | 9 | Yosemite cliff scaled by 15- and 48-Across: 2 wds. |
| 44% | VIDEOVANGUARD | 13 | Achievement award won by 17-Across in 1987 (it was renamed in 1991 for Michael Jackson): 2 wds. |
| 43% | NNEDIOKORAFOR | 13 | 15-Across and 32-Across novelist who won a Hugo Award and a Nebula Award for "Binti" (2 wds.) |
| 43% | NEWTSCAMANDER | 13 | Character played by 15-Across in "Fantastic Beasts and Where to Find Them": 2 wds. |
| 42% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 42% | PULITZERPRIZE | 13 | Prestigious award won in 2018 by "DAMN.": 2 wds. |
| 41% | MVP | 3 | Award won by 52-Across in 1949 |
| 41% | VANGOGH | 7 | Dutch artist portrayed by 15-Across, 20-Across, and 34-Across: 2 wds. |
| 41% | YOUBABY | 7 | 1966 song and album by 15-Across: 2 wds. |
| 40% | THEMATCH | 8 | 2020 team charity golf event won by 1-Across/55-Across and 15-Across (2 wds.) |
| 40% | DAVIDOYELOWO | 12 | 19-Across and 33-Across actor who won a 2015 NAACP Image Award for his portrayal of Martin Luther King Jr. in "Selma" (2 wds.) |
| 40% | GLORIAGAYNOR | 12 | 43-Across singer who won the only 19-Across/36-Across Grammy Award (2 wds.) |
| 39% | WILDTHOUGHTS | 12 | 2017 #2 hit by 15-Across featuring Rihanna and Bryson Tiller: 2 wds. |
| 39% | GOLDMEDAL | 9 | Olympic honor won six times by 15-Across: 2 wds. |
| 39% | GLOVE | 5 | Gold ___ (fielding award won by 14-Across in 2002 and 2003) |
| 39% | KISSMEKATE | 10 | 1948 show with music and lyrics by 39-Across that won the first Tony Award for Best Musical (3 wds.) |
| 38% | ANNPATCHETT | 11 | 15-Across and 43-Across writer who won the Orange Prize for Fiction and the PEN/Faulkner Award for Fiction for "Bel Canto" (2 wds.) |