| Hint | # | Answer | % Correct |
|---|---|---|---|
| Most French Open titles | 14 | Rafael Nadal | 97%
|
| Most Grand Slams in the 2000s (decade) | 15 | Roger Federer | 97%
|
| Most weeks at #1 | 428 | Novak Djokovic | 95%
|
| Only British player to win Wimbledon | (2013, 2016) | Andy Murray | 84%
|
| Husband/wife pair with the most combined Grand Slam singles titles | 30 | Andre Agassi / Steffi Graf | 76%
|
| Most Grand Slams in the 1990s | 12 | Pete Sampras | 73%
|
| Most Grand Slams in the 1970s | 8 | Björn Borg | 68%
|
| Most combined singles and doubles titles | 155 | John McEnroe | 68%
|
| Most recent American to win a Grand Slam title | U.S. Open (2003) | Andy Roddick | 54%
|
| Youngest player to reach #1 | 19 yrs | Carlos Alcaraz | 54%
|
| Only black player to win Wimbledon | (1975) | Arthur Ashe | 50%
|
| Most Grand Slams in the 1980s | 7 | Mats Wilander / Ivan Lendl | 47%
|
| Most singles titles | 109 | Jimmy Connors | 46%
|
| Most aces hit in one match | 113 | John Isner | 46%
|
| Only player to win a calendar year Grand Slam | (1969) | Rod Laver | 46%
|
| Most fines in a single match | $113,000 | Nick Kyrgios | 42%
|
| Tallest player to win a Grand Slam title | 6'6" (1.98 meters) | Juan Martin Del Potro / Marin Čilić / Daniil Medvedev | 41%
|
| Only player to win a Grand Slam as a wild card | Wimbledon (2001) | Goran Ivanišević | 36%
|
| Youngest to win a Grand Slam title | 17 yrs | Michael Chang | 32%
|