| 100% | DISQUALIFIED | 12 | Ineligible for a prize, like Maximum Security, the horse who crossed the finish line first in the 2019 29-Across |
| 38% | LAST | 4 | Like one who crossed the line after everyone, in a race |
| 35% | EDITHWHARTON | 12 | 13-Across and 25-Across writer who was the first woman to win a Pulitzer Prize in Literature, for her 1920 novel "The Age of Innocence" (2 wds.) |
| 31% | AWAY | 4 | Like the winning team in every World Series game, for the first time ever (October, 2019) |
| 31% | WON | 3 | Crossed the finish line first |
| 31% | WIN | 3 | Cross the finish line first |
| 31% | RACHELWEISZ | 11 | "The Lobster" actress who was nominated for a 2019 Golden Globe Award for her role in 40-Across (2 wds.) |
| 31% | SAMMENDES | 9 | "The Ferryman" director who won the Tony Award for Best Direction of a Play in 2019 (2 wds.) |
| 31% | WON | 3 | Crossed the finish line first, say |
| 31% | BOBMACKIE | 9 | "The Cher Show" costumer who won the 2019 Tony Award for Best Costume Design in a Musical (2 wds.) |
| 30% | BRYANCRANSTON | 13 | "Network" actor who won the Tony Award for Best Performance by a Leading Actor in a Play in 2019 (2 wds.) |
| 30% | SANTINO | 7 | With 38-Across, "Tootsie" actor who won the 2019 Tony Award for Best Performance by a Leading Actor in a Musical |
| 30% | OLIVIACOLMAN | 12 | "The Lobster" actress who won a 2019 Golden Globe Award for her role in 40-Across (2 wds.) |
| 30% | CHLOEZHAO | 9 | 16-Across director who won an Academy Award for Best Director in 2021, becoming the first non-white woman to win a directing Oscar (2 wds.) |
| 30% | ELAINEMAY | 9 | "The Waverly Gallery" actress who won the Tony Award for Best Performance by a Leading Actress in a Play in 2019 (2 wds.) |
| 29% | EDITH | 5 | Wharton who was the first woman to win a Pulitzer Prize for fiction |
| 29% | ANNAQUINDLEN | 12 | "One True Thing," 14-Across, and 26-Across/29-Across novelist who won the Pulitzer Prize for Commentary in 1992 (2 wds.) |
| 29% | ASINGLETHREAD | 13 | 2019 novel by 34-Across about the women who embroidered the kneelers for Winchester Cathedral in the 1930s (3 wds.) |
| 29% | OUT | 3 | ___ of Bounds, term for a player who touches any boundary line in the NFL |
| 29% | ALISTROKER | 10 | Actress who won a Tony for her role as Ado Annie in the 2019 Broadway revival of "Oklahoma!": 2 wds. |
| 29% | ZACHARYGORDON | 13 | Child actor who played 40-Across in the first three "Diary of a Wimpy Kid" films (2 wds.) |
| 28% | WON | 3 | Was the first to cross the finish line |
| 28% | ANGELA | 6 | Bassett who was the first person to be nominated for an Oscar for acting in a Marvel movie |
| 28% | KATRINALENK | 11 | 30-Across singer/actress who won the 2018 Tony Award for Best Actress in a Musical (2 wds.) |
| 28% | DAVECHAPPELLE | 13 | "A Star Is Born" actor who won the Mark Twain Prize in 2019: 2 wds. |
| 28% | JAMESPALLISON | 13 | American immunologist who won the 2018 Nobel Prize in Physiology or Medicine with Tasuku Honjo for discovery of a cancer therapy: 3 wds. |
| 28% | NBA | 3 | Org. embroiled in scandal after a general manager tweeted support for the 16-Across protests (October, 2019) |
| 28% | ALSORAN | 7 | Horse that fails to finish first, second, or third in a race (Hyph.) |
| 27% | RAMIMALEK | 9 | Actor who became the first one of Egyptian heritage to win an Oscar for Best Actor in 2019: 2 wds. |
| 27% | OHIOSTATE | 9 | Big Ten East football team who played the University of Washington in the 2019 49-Across (2 wds.) |