| 100% | PULITZERPRIZE | 13 | Award won by 18-Across for "Beloved" (2 wds.) |
| 83% | PULITZERPRIZE | 13 | Award won by 40-Across for 18-Across (2 wds.) |
| 77% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 75% | PULITZERPRIZE | 13 | Award won by 18-Across (2 wds.) |
| 70% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 69% | VIDEOVANGUARD | 13 | Achievement award won by 17-Across in 1987 (it was renamed in 1991 for Michael Jackson): 2 wds. |
| 65% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 64% | PULITZERPRIZE | 13 | Prestigious award for authors, won by 42-Across for her first novel: 2 wds. |
| 62% | EMMYAWARD | 9 | Honor won twice by 18-Across in the 1950s for playing Schultzy on "The Bob Cummings Show": 2 wds. |
| 60% | BESTACTOR | 9 | Oscar won by 21-Across for "The King's Speech": 2 wds. |
| 60% | BESTFOLKALBUM | 13 | 2012 Grammy won by 44-Across for 18-Across: 3 wds. |
| 60% | SILVERSLUGGER | 13 | NL batting award won by 14-Across in 2000, 2002, and 2003: 2 wds. |
| 60% | JULIANFELLOWES | 14 | 18-Across and 44-Across writer/creator who won an Academy Award for Best Original Screenplay for "Gosford Park" (2 wds.) |
| 60% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 60% | LEIGHBARDUGO | 12 | 18-Across and 29-Across writer whose novel "Ninth House" won the 2019 Goodreads Choice Award for Best Fantasy (2 wds.) |
| 59% | SILVERSLUGGER | 13 | Hitting award won five times by 15-Across, including in 2013: 2 wds. |
| 59% | EMILYHENRY | 10 | 18-Across, 26-Across, and 35-Across novelist who won the 2021, 2022, and 2023 Goodreads Choice Award for Best Romance (2 wds.) |
| 58% | SILVERSLUGGER | 13 | Batting award won four times by 17-Across and once by 39-Across: 2 wds. |
| 58% | NOBELPRIZE | 10 | Award 18-Across won twice, for her work in physics and chemistry: 2 wds. |
| 57% | JANEHARPER | 10 | 18-Across and 33-Across writer whose novel "The Dry" won the British Book Award for Crime & Thriller Book of the Year 2018 (2 wds.) |
| 57% | EMMY | 4 | Award won by 68 Across Rickman for "Rasputin" (is there an echo in here?) |
| 56% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 54% | JULIANNEMOORE | 13 | 18-Across actress who won an Oscar for 39-Across (2 wds.) |
| 54% | MYCOUSINVINNY | 13 | 1992 courtroom comedy for which 18-Across won an Academy Award: 3 wds. |
| 53% | RULEOFWOLVES | 12 | Novel by 40-Across that won the 2021 Goodreads Choice Award for Young Adult Fantasy (3 wds.) |
| 53% | TRIPLECROWN | 11 | Batting feat achieved twice by 18-Across: 2 wds. |
| 53% | SHOOTINGGUARD | 13 | Position played by 18-Across: 2 wds. |
| 53% | KILLINTIME | 10 | Album by 45-Across featuring the singles 18-Across and 26-Across that won the 1989 Album of the Year Academy of Country Music Award (2 wds.) |
| 53% | PORKANDBEANS | 12 | Single by 42-Across whose video won a Grammy Award for Best Music Video in 2009 (3 wds.) |
| 53% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |