| 100% | SERENAWILLIAMS | 14 | 27-/37-Across won her first Grand Slam title (the 2018 US Open) by defeating this tennis legend: 2 wds. |
| 47% | AUSTRALIANOPEN | 14 | In 2019, 27-/37-Across won her second Grand Slam title at this Melbourne tournament: 2 wds. |
| 40% | SOFIAKENIN | 10 | American tennis player who won her first major title at the 2020 Australian Open: 2 wds. |
| 40% | IGASWIATEK | 10 | Polish tennis player who won her first major title at the 2020 French Open: 2 wds. |
| 39% | NAOMIOSAKA | 10 | Tennis star who won her first two Grand Slams in consecutive tournaments (2018-2019): 2 wds. |
| 37% | VENUSWILLIAMS | 13 | Tennis star who won her first two Grand Slams in consecutive tournaments (2000): 2 wds. |
| 37% | CHRISEVERT | 10 | Tennis star who won her first two Grand Slams in consecutive tournaments (1974): 2 wds. |
| 36% | MONICASELES | 11 | Left-handed tennis player who won the last of her nine Grand Slam titles in 1996: 2 wds. |
| 36% | DOMINICTHIEM | 12 | Austrian tennis player who won his first major title at the 2020 US Open: 2 wds. |
| 35% | STEFFIGRAF | 10 | Her Open Era record of 22 Grand Slam singles titles was broken by 35-Across in 2017: 2 wds. |
| 34% | JOHNMCENROE | 11 | Left-handed tennis player from the US who won seven Grand Slam singles titles: 2 wds. |
| 34% | JIMMYCONNORS | 12 | Left-handed tennis player from the US who won eight Grand Slam singles titles: 2 wds. |
| 34% | MARGARETCOURT | 13 | Australian tennis player who was the first woman to win the Grand Slam in the Open Era: 2 wds. |
| 32% | SIMONAHALEP | 11 | Romanian professional tennis player who won 2 Grand Slam singles titles in her career: 2 wds. |
| 32% | SERENAWILLIAMS | 14 | She has the Open Era record of 23 Grand Slam singles titles, more than any woman or man: 2 wds. |
| 31% | VENUSWILLIAMS | 13 | American professional tennis player who won 14 Grand Slam Women's doubles titles in her career: 2 wds. |
| 29% | MARTINAHINGIS | 13 | Swiss tennis player who won the US Open in 1997: 2 wds. |
| 29% | STANWAWRINKA | 12 | Swiss tennis player who won the US Open in 2016: 2 wds. |
| 28% | EMMARADUCANU | 12 | British tennis player who was unseeded when she won the 2021 US Open at age 18 (2 wds.) |
| 28% | ROGERFEDERER | 12 | Swiss tennis player who won the US Open from 2004 to 2008: 2 wds. |
| 28% | NOVAKDJOKOVIC | 13 | Serbian tennis star who has won 12 Grand Slam singles titles: 2 wds. |
| 28% | PETESAMPRAS | 11 | American former professional tennis player who won 14 Grand Slam titles during his career: 2 wds. |
| 27% | CHRISEVERT | 10 | American tennis player who achieved the Career Grand Slam twice in her career: 2 wds. |
| 27% | ANDYMURRAY | 10 | Scottish tennis player defeated by 32-Across in the 2016 Australian Open finals: 2 wds. |
| 27% | ROGERFEDERER | 12 | Swiss tennis pro with 20 singles Grand Slam titles, who was the sixth player to achieve the Career Grand Slam: 2 wds. |
| 27% | BOBBRYAN | 8 | Tennis player who won 16 Grand Slam doubles titles and a 2012 Olympic gold medal with his twin brother, Mike: 2 wds. |
| 27% | NADAL | 5 | Winner of the 2018 French Open, his 17th Grand Slam title |
| 27% | SERENAWILLIAMS | 14 | American tennis player who achieved the Career Grand Slam three times in her career: 2 wds. |
| 27% | STEFFIGRAF | 10 | German tennis player who achieved the Career Grand Slam four times in her career: 2 wds. |
| 27% | PETE | 4 | ___ Sampras, retired tennis legend and former world no.1 who won 14 grand slam singles titles |