| 100% | MARTINAHINGIS | 13 | Partner of 18-Across in Ladies' Doubles at Wimbledon in 1998 (and Ladies' Singles champion of 1997) (2 wds.) |
| 63% | JANANOVOTNA | 11 | Winner of the Ladies' Singles and Doubles championships at Wimbledon in 1998 (2 wds.) |
| 47% | PETESAMPRAS | 11 | Winner of the Gentlemen's Singles championship at Wimbledon in 1998 (2 wds.) |
| 42% | TARALIPINSKI | 12 | American figure skater who won gold in ladies' singles at the 1998 Olympic Games: 2 wds. |
| 39% | ANDYMURRAY | 10 | British tennis player who won the men's singles title at Wimbledon in 2013 and 2016 (2 wds.) |
| 39% | ANNETTEBENING | 13 | Actress and wife of 18-Across, who also appears in "Rules Don't Apply": 2 wds. |
| 38% | LEOPOLDBLOOM | 12 | Partner of 31-Across portrayed by Gene Wilder in 1967 and Matthew Broderick in 2005: 2 wds. |
| 37% | MIKETYSON | 9 | American former boxer who became the youngest heavyweight champion in history in 1986 at the age of 20 years and 4 months: 2 wds. |
| 37% | SHOELESSJOE | 11 | Nickname of "Black Sox" outfielder Jackson who's a character in 18-Across and 32-Across: 2 wds. |
| 35% | JOHNSINGLETON | 13 | Director of 18-Across and 40-Across who passed away in 2019 (2 wds.) |
| 35% | MANDYPATINKIN | 13 | "Homeland" actor who received cornea transplants in 1997 and 1998: 2 wds. |
| 35% | SNAKEEYES | 9 | Roll of double ones at the craps table, in slang: 2 wds. |
| 35% | NAOMIOSAKA | 10 | Japanese-American tennis player who was the Women's Singles champion at the Australian Open in 2019 and 2021 (2 wds.) |
| 35% | JAMESHONG | 9 | Portrayer of Gong Gong in "Everything Everywhere All at Once" and Jade Emperor on "American Born Chinese": 2 wds. |
| 35% | STEPHANIEHSU | 12 | Portrayer of Joy Wang in "Everything Everywhere All at Once" and Shiji Niangniang on "American Born Chinese": 2 wds. |
| 35% | SARAHHUGHES | 11 | American figure skater who won gold in ladies' singles at the 2002 Olympic Games: 2 wds. |
| 35% | CONORMCGREGOR | 13 | UFC champion in two different weight classes, and the highest-paid athlete of 2021: 2 wds. |
| 34% | LEANNRIMES | 10 | Singer whose "How Do I Live" spent 32 weeks in the Billboard Top 10 in 1997 and 1998: 2 wds. |
| 34% | MICHELLEYEOH | 12 | Portrayer of Evelyn Wang in "Everything Everywhere All at Once" and Guanyin on "American Born Chinese": 2 wds. |
| 34% | PATRICKRAFTER | 13 | Australian tennis player who won back-to-back US Opens in 1997 and 1998: 2 wds. |
| 34% | MIKETYSON | 9 | Former boxing star found guilty in 1992, 1998, 2004, and 2007 of criminal conduct: 2 wds. |
| 34% | ROUNDTABLE | 10 | Meeting place of 18-Across and his knights: 2 wds. |
| 34% | ANDRAECROUCH | 12 | "Soon and Very Soon" singer who was inducted into the Gospel Music Hall of Fame in 1998: 2 wds. |
| 34% | HOLLANDTAYLOR | 13 | "Two and a Half Men" actress who came out of the closet in 2015 at age 72: 2 wds. |
| 34% | KENJENNINGS | 11 | "Jeopardy!" champion and host who was inducted into the Jeopardy! Hall of Fame in 2025: 2 wds. |
| 33% | WALTERMATTHAU | 13 | Jack Lemmon's costar in 18- and 37-Across: 2 wds. |
| 33% | JOHNLENNON | 10 | 32-Across' songwriting partner in 18-Across: 2 wds. |
| 33% | STEPHENKING | 11 | Author of "The Shining" and 18-Across: 2 wds. |
| 33% | RICHARDGERE | 11 | Costar of Julia Roberts in 18-Across: 2 wds. |
| 33% | NOBELPRIZE | 10 | Award 18-Across won twice, for her work in physics and chemistry: 2 wds. |