| 100% | JULIAROBERTS | 12 | Best Actress Oscar winner for 32-Across (2 wds.) |
| 80% | RENEEZELLWEGER | 14 | Best Actress Oscar winner for the 2019 film "Judy": 2 wds. |
| 75% | SANDRABULLOCK | 13 | Best Actress Oscar winner for "The Blind Side" who was a Worst Actress Razzie winner for "All About Steve": 2 wds. |
| 74% | MERYLSTREEP | 11 | 1982 Best Actress Oscar winner for "Sophie's Choice" (2 wds.) |
| 73% | HOLLYHUNTER | 11 | Best Actress Oscar winner for her role in the 1993 film "The Piano" (2 wds.) |
| 73% | LAURADERN | 9 | Best Supporting Actress Oscar winner for the 2019 film "Marriage Story": 2 wds. |
| 71% | CATEBLANCHETT | 13 | Best Actress Oscar winner over Meryl Streep (for 2013's "Blue Jasmine"): 2 wds. |
| 70% | LAURADERN | 9 | Best Actress Oscar nominee for 29-Across (2 wds.) |
| 70% | SUSANSARANDON | 13 | Best Actress Oscar winner over Meryl Streep (for 1995's "Dead Man Walking"): 2 wds. |
| 70% | SANDRABULLOCK | 13 | Best Actress Oscar winner over Meryl Streep (for 2009's "The Blind Side"): 2 wds. |
| 67% | EVAMARIE | 8 | ___ Saint (Best Supporting Actress Oscar winner for 1954's "On the Waterfront"): 2 wds. |
| 66% | JESSICALANGE | 12 | 1982 Best Supporting Actress Oscar winner for "Tootsie" (2 wds.) |
| 65% | DIANEKEATON | 11 | Winner of a Best Actress Oscar for playing Annie Hall, the title role of 1977's Best Picture: 2 wds. |
| 65% | ALFONSOCUARON | 13 | Best Director Oscar winner for the 2018 film "Roma": 2 wds. |
| 64% | HILARYSWANK | 11 | Two-time Best Actress Oscar winner who plays Bridget in 46-Across (2 wds.) |
| 64% | INGRIDBERGMAN | 13 | Winner of a Best Actress Oscar for "Gaslight" and a Best Supporting Actress Oscar for "Murder on the Orient Express": 2 wds. |
| 63% | DIANELADD | 9 | Best Supporting Actress Oscar nominee for 29-Across (2 wds.) |
| 63% | KATEWINSLET | 11 | "Titanic" Best Actress Oscar winner (2 wds.) |
| 63% | ALBERTFINNEY | 12 | Best Supporting Actor Oscar nominee for 32-Across (2 wds.) |
| 63% | MAGGIESMITH | 11 | Winner of a Best Actress Oscar for "The Prime of Miss Jean Brodie" and a Best Supporting Actress Oscar for "California Suite": 2 wds. |
| 63% | CHER | 4 | Best Actress Oscar winner for "Moonstruck" |
| 62% | JODIEFOSTER | 11 | Two-time Best Actress Oscar winner who plays Liz Danvers in season 4 of 43-Across (2 wds.) |
| 62% | ANTHONYHOPKINS | 14 | Best Actor Oscar winner for both "The Silence of the Lambs" and "The Father": 2 wds. |
| 61% | DANIELDAYLEWIS | 14 | Best Actor Oscar winner for "My Left Foot," "There Will Be Blood," and "Lincoln": 2 wds., hyph. |
| 61% | BRENDANFRASER | 13 | 2023 Best Actor Oscar winner for his role in "The Whale": 2 wds. |
| 61% | JENNIFER | 8 | With 48-Across, Best Actress Oscar winner for "Silver Linings Playbook" |
| 60% | SANDRABULLOCK | 13 | "The Blind Side" Best Actress Oscar winner who starred in 15-Across, 24-Across, 31-Across, and 40-Across (2 wds.) |
| 60% | HELENHUNT | 9 | Best Actress Oscar winner for As Good as it Gets |
| 60% | JESSICALANGE | 12 | She won a Best Actress Oscar for "Blue Sky" and Best Supporting Actress for "Tootsie": 2 wds. |
| 60% | RAINMAN | 7 | 1988 Oscar winner for Best Picture (2 wds.) |