| 100% | SQUAREPEG | 9 | Something that won't fit in a round hole: 2 wds. |
| 69% | PEG | 3 | Square thing that won't fit in a round hole |
| 55% | PEG | 3 | A square one won’t fit in a round hole |
| 54% | SQUAREPEG | 9 | Item that can’t fit in a round hole, in an idiom |
| 46% | PEG | 3 | A square one doesn't fit in a round hole |
| 46% | ISLE | 4 | Key that doesn't fit in a hole? |
| 45% | TAKINGTHE | 9 | "___ Long Way," country album by The Chicks that won a Grammy Award in 2007: 2 wds. |
| 44% | WEREHERE | 8 | HBO reality show, where drag queens visit small-town America, that won a Peabody Award in 2023: 2 wds. |
| 43% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 43% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 42% | OAR | 3 | Something that fits in a lock |
| 40% | ICEPACK | 7 | Item in a freezer that reduces swelling: 2 wds. |
| 40% | PEG | 3 | You can't fit a square __ in a round hole |
| 40% | DENVERBRONCOS | 13 | Team that won Super Bowl 50 in 2016: 2 wds. |
| 39% | SCHITTSCREEK | 12 | Canadian sitcom created by 26-Across and his son Daniel that won a record seven Emmys in 2020 (2 wds.) |
| 39% | PEG | 3 | Wooden piece that fits in a hole |
| 39% | THECROWN | 8 | Historical drama series that won four Golden Globes in 2021: 2 wds. |
| 38% | BETTERCALLSAUL | 14 | AMC "Breaking Bad" prequel that won a Peabody Award in 2023: 3 wds. |
| 38% | NURSEJACKIE | 11 | Showtime comedy-drama set in a hospital that ended this summer: 2 wds. |
| 38% | DEBITCARD | 9 | Payment option in a wallet that's neither cash nor credit: 2 wds. |
| 38% | ESSAYTEST | 9 | Exam that's sometimes written in a blue book: 2 wds. |
| 38% | PEG | 3 | Square ___ in a round hole |
| 38% | PEG | 3 | "Square ___ in a round hole" |
| 38% | HOLIDAYINN | 10 | 1942 film that won a Best Original Song Oscar for 34-Across: 2 wds. |
| 38% | SQUIDGAME | 9 | Netflix series created by Hwang Dong-hyuk that won an Emmy Award for Outstanding Directing for a Drama Series in 2022 (2 wds.) |
| 38% | DRNO | 4 | Villain with the title role in a 1962 movie that introduced 007: 2 wds. |
| 38% | ICECREAM | 8 | Dessert that might be served in a cone: 2 wds. |
| 38% | MISFIT | 6 | Square peg in a round hole |
| 38% | PEG | 3 | Square ___ in a round hole (misfit) |
| 38% | CULTURECLUB | 11 | "Karma Chameleon" band that won the Grammy for Best New Artist in 1984: 2 wds. |