| Hint | Player | % Correct |
|---|---|---|
| Beats Nadal in the fourth round of the 2009 French Open | Robin Soderling | 84%
|
| Ranked 44th, he wins the men's French Open in 2004 | Gaston Gaudio | 69%
|
| Beats Ivan Lendl in the fourth round of the French Open in 1989 | Michael Chang | 64%
|
| Beats Nadal in the second round of Wimbledon in 2012 | Lukas Rosol | 60%
|
| Wins the women's Olympics in 2016 | Monica Puig | 60%
|
| Beats Sampras in the quarters and goes on to win Wimbledon in1996 | Richard Krajicek | 60%
|
| Beats Djokovic in the second round of the 2017 Australian Open | Denis Istomin | 58%
|
| Beats Serena in the semis of the 2015 US Open | Roberta Vinci | 58%
|
| Beats Djokovic in the third round of Wimbledon 2016 | Sam Querrey | 53%
|
| Wins the women's French Open in 2004 | Anastasia Myskina | 47%
|
| Beats Serena in the first round of the 2012 French Open | Virginie Razzano | 40%
|
| Beats Martina Hingis in the 1997 French Open final | Iva Majoli | 38%
|
| Beats Justine Henin in Wimledon 2007's semis | Marion Bartoli | 38%
|
| Beats Navratilova in the 4th round of the 1988 French Open | Natasha Zvereva | 13%
|
| Beats defending champion McEnroe in the quarters of Wimledon 1985 | Kevin Curren | 11%
|
| Beats two-time defending champion Becker in the second round of Wimbledon 1987 | Peter Doohan | 11%
|