| 100% | SILVERSLUGGER | 13 | Award that 17-Across won four times: 2 wds. |
| 72% | SILVERSLUGGER | 13 | Batting award won four times by 17-Across and once by 39-Across: 2 wds. |
| 65% | GRAMMYAWARD | 11 | Prize that 17-Across won three times for her spoken-word albums: 2 wds. |
| 57% | OSCAR | 5 | Award that Katharine Hepburn won four times |
| 56% | PULITZERPRIZE | 13 | Award that 14-Across won twice, for "Fences" and "The Piano Lesson": 2 wds. |
| 56% | WORLDSERIES | 11 | Championship that 17-Across won twice, with the A's and Yankees: 2 wds. |
| 55% | BESTDIRECTOR | 12 | Oscar won four times by John Ford: 2 wds. |
| 53% | THEAMERICANS | 12 | Spy drama starring 17-Across and 41-Across that won the 2019 Golden Globe Award for Best Television Series - Drama (2 wds.) |
| 49% | SPINGARNMEDAL | 13 | NAACP award that John Lewis won in 2002: 2 wds. |
| 48% | TRAILBLAZERS | 12 | Portland NBA team that 17-Across owned: 2 wds. |
| 47% | DAWNSTALEY | 10 | Basketball Hall of Fame inductee who won four Coach of the Year awards in 2020: 2 wds. |
| 47% | LALAW | 5 | Legal show that won the Emmy for Outstanding Drama Series four times: 2 wds., abbr. |
| 46% | DCUNITED | 8 | Washington team that has won the MLS Cup four times (2 wds.) |
| 46% | GRAMMYS | 7 | Awards won 17 times by 16-Across |
| 46% | SILVERSLUGGER | 13 | Hitting award won five times by 15-Across, including in 2013: 2 wds. |
| 44% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 43% | THECROWN | 8 | Historical drama series that won four Golden Globes in 2021: 2 wds. |
| 42% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 42% | HARLANCOBEN | 11 | 17-Across and 30-Across novelist who is the first writer to win an Anthony Award, a Shamus Award, and an Edgar Award (2 wds.) |
| 41% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 41% | LONELYBOY | 9 | 27-Across song that won two Grammy Awards in 2013 (2 wds.) |
| 41% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 41% | ALLISONJANNEY | 13 | "Mom" star who won four Emmy Awards for playing C.J. Cregg on "The West Wing" (2 wds.) |
| 41% | EMMY | 4 | Award won four times by Jim Parsons for "The Big Bang Theory" |
| 40% | ESPY | 4 | TV athletic award that Tiger Woods has won 21 times |
| 40% | GOLDMEDAL | 9 | Olympic honor won six times by 15-Across: 2 wds. |
| 40% | THEECHOMAKER | 12 | 2006 novel by 32-Across that won the National Book Award for Fiction (3 wds.) |
| 40% | THEROUNDHOUSE | 13 | 2012 Novel by 44-Across that won a National Book Award for Fiction (3 wds.) |
| 40% | USWOMENSOPEN | 12 | Major golf championship won four times each by Betsy Rawls and Mickey Wright (3 wds.) |
| 40% | RIOOLYMPICS | 11 | International competition where 40-Across won four gold medals in 2016 (2 wds.) |