| 100% | ONEDIRECTION | 12 | "Drag Me Down" group that won 14-Across in 2013: 2 wds. |
| 51% | SAMSMITH | 8 | "Stay With Me" singer who won 14-Across in 2015: 2 wds. |
| 45% | FETTYWAP | 8 | "Trap Queen" singer who won 14-Across in 2016: 2 wds. |
| 43% | IMNOT | 5 | With 49-Across, song that won 14-Across his Best Country Song Grammy: 2 wds. |
| 42% | THEOPEN | 7 | Major golf tournament that 30-Across won in Scotland in 2013: 2 wds. |
| 41% | BREAKINGBAD | 11 | AMC crime show that won Primetime Emmys for Outstanding Drama Series in 2013 and 2014 (2 wds.) |
| 41% | LONELYBOY | 9 | 27-Across song that won two Grammy Awards in 2013 (2 wds.) |
| 41% | PROCOLHARUM | 11 | "A Whiter Shade of Pale" group that turned down Woodstock: 2 wds. |
| 40% | LEDZEPPELIN | 11 | "Stairway to Heaven" group that turned down Woodstock: 2 wds. |
| 40% | LYNYRDSKYNYRD | 13 | Rock group that released "Free Bird" in 1974: 2 wds. |
| 40% | CELTICTHUNDER | 13 | Irish vocal group that won Billboard's Top World Album Artist award three times: 2 wds. |
| 40% | LITTLEBIG | 9 | ___ Town, country music group that won a Grammy for their hit song "Girl Crush": 2 wds. |
| 39% | HOUSTONASTROS | 13 | AL West team that lost 111 games in 2013, then won the World Series four years later: 2 wds. |
| 39% | VILLAGEPEOPLE | 13 | Group that had a #2 hit in 1979 with "Y.M.C.A.": 2 wds. |
| 38% | USAIR | 5 | Aviation company that merged with American in 2013: 2 wds. |
| 38% | SPICEGIRLS | 10 | Group that made up the phrase "zig-a-zig-ah" in their 1997 hit "Wannabe": 2 wds. |
| 38% | THEGODFATHER | 12 | Oscar-winning film starring 14-Across and 28-Across that debuted in March 1972 (2 wds.) |
| 38% | SQUAREPEG | 9 | Something that won't fit in a round hole: 2 wds. |
| 37% | INDIANAFEVER | 12 | Midwestern WNBA team that won the title in 2012: 2 wds. |
| 37% | DENVERBRONCOS | 13 | Team that won Super Bowl 50 in 2016: 2 wds. |
| 37% | THEAVENGERS | 11 | Superhero film by Joss Whedon that won the 2013 Hugo Award for Best Dramatic Presentation: 2 wds. |
| 37% | VENUSWILLIAMS | 13 | American professional tennis player who won 14 Grand Slam Women's doubles titles in her career: 2 wds. |
| 37% | OLDDOMINION | 11 | "Written in the Sand" band that won Vocal Group of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 36% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 36% | THECROWN | 8 | Historical drama series that won four Golden Globes in 2021: 2 wds. |
| 36% | TRUEGRIT | 8 | 1969 Western that won 44-Across an Oscar: 2 wds. |
| 36% | DENVERNUGGETS | 13 | Northwest Division team that won the franchise's first-ever NBA Championship in 2023, after 56 years: 2 wds. |
| 36% | TEXASRANGERS | 12 | AL West team that won the franchise's first-ever World Series in 2023, after 62 years: 2 wds. |
| 36% | EASYA | 5 | Class that won't bring down one's GPA (2 wds.) |
| 36% | BEEGEES | 7 | Musical group that recorded 16-, 21-, and 41-Across: 2 wds. |