| 100% | THEMATCH | 8 | 2020 team charity golf event won by 1-Across/55-Across and 15-Across (2 wds.) |
| 43% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 43% | ACADEMYAWARDS | 13 | Golden statuettes won by 15- and 26-/34-Across during a February 22 ceremony: 2 wds. |
| 39% | FLOOREXERCISE | 13 | Gymnastics event won by 40-Across at the 18-Across and five times at the World Championships (2 wds.) |
| 39% | YOUBABY | 7 | 1966 song and album by 15-Across: 2 wds. |
| 38% | GOLDMEDAL | 9 | Olympic honor won six times by 15-Across: 2 wds. |
| 38% | ELCAPITAN | 9 | Yosemite cliff scaled by 15- and 48-Across: 2 wds. |
| 38% | TONYAWARD | 9 | 2005 Broadway honor won by 15-Across: 2 wds. |
| 38% | SILVERSLUGGER | 13 | NL batting award won by 14-Across in 2000, 2002, and 2003: 2 wds. |
| 37% | SILVERSLUGGER | 13 | Batting award won four times by 17-Across and once by 39-Across: 2 wds. |
| 36% | CIAAGENT | 8 | Job held by the four characters from 15-, 19-, 31-, and 40-Across: 2 wds. |
| 36% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 36% | HOUSTONCOMETS | 13 | WNBA team that 15- and 30-Across played for: 2 wds. |
| 36% | MICHAELPHELPS | 13 | American swimmer who won 3 relay Golds in 2016 by breaking the Olympic Record in 3 team events: 2 wds. |
| 36% | SCHITTSCREEK | 12 | Canadian sitcom created by 26-Across and his son Daniel that won a record seven Emmys in 2020 (2 wds.) |
| 36% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 36% | ARCHIEGRIFFIN | 13 | Only player to win the 15-Across twice, in 1974 and 1975: 2 wds. |
| 36% | STUCKWITH | 9 | "___ U," song by Ariana Grande and Justin Bieber (birthday today) which won an MTV Video Music Award in 2020: 2 wds. |
| 36% | TOMBRADY | 8 | Buccaneers quarterback who teamed with Packers quarterback Aaron Rodgers on June 1 for 15-Across: 2 wds. |
| 36% | PATRICKMAHOMES | 14 | Chiefs quarterback who teamed with Bills quarterback Josh Allen on June 1 for 15-Across: 2 wds. |
| 35% | VANGOGH | 7 | Dutch artist portrayed by 15-Across, 20-Across, and 34-Across: 2 wds. |
| 35% | SILVERSLUGGER | 13 | Hitting award won five times by 15-Across, including in 2013: 2 wds. |
| 35% | WILDTHOUGHTS | 12 | 2017 #2 hit by 15-Across featuring Rihanna and Bryson Tiller: 2 wds. |
| 35% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 35% | NEWTSCAMANDER | 13 | Character played by 15-Across in "Fantastic Beasts and Where to Find Them": 2 wds. |
| 34% | POLEVAULT | 9 | 2020 Olympic event won by Armand Duplantis and Katie Moon in their respective competitions |
| 34% | TEAPARTY | 8 | Event attended by Alice and the Mad Hatter: 2 wds. |
| 34% | MYSTICRIVER | 11 | 2003 movie set in Boston, for which Sean Penn and Tim Robbins each won a 1-Across: 2 wds. |
| 34% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |
| 34% | GLORIASTEINEM | 13 | Feminist journalist played by 15-Across and Alicia Vikander in a 2020 biopic based on the memoir "My Life on the Road" (2 wds.) |