| Hint | Answer | % Correct |
|---|---|---|
| Player who he beat to win his first Grand Slam title | Jo-Wilfried Tsonga | 80%
|
| Number of losses in 2015 | Six | 77%
|
| Number of titles in 2015 | Eleven | 73%
|
| Player who beat him in the 2014 US Open semifinals | Kei Nishikori | 60%
|
| Player who beat him in his first Grand Slam match ever | Marat Safin | 53%
|
| Number of consecutive victories before Federer beat him at the French Open | 41 | 50%
|
| Player who he beat 6:0,6:2 in the Beijing finals | Tomas Berdych | 47%
|
| Number of victories in 2015 | 82 | 43%
|
| Player who he beat to win his first title in Dubai | David Ferrer | 40%
|
| He retired in the Serbia Open quarterfinals against this Serbian player | Filip Krajinović | 37%
|
| Player who beat him in Doha in 2015 | Ivo Karlović | 33%
|
| First match ever against Rafael Nadal (tournament and year) | Roland Garros 2006 | 30%
|
| First match ever against Roger Federer (tournament and year) | Monte Carlo Masters 2006 | 27%
|
| Player who he beat to win his first ATP title | Nicolas Massu | 27%
|
| Player who he beat to win his first ATP Masters 1000 title | Guillermo Canas | 23%
|
| First match ever on the ATP World Tour against Andy Murray (tournament and year) | Madrid Open 2006 | 23%
|
| Player who he beat to win his first title in Beijing | Marin Čilić | 23%
|
| Player who he beat to win his second title in the Serbia Open | Feliciano Lopez | 20%
|
| He won his only doubles title in Queen's Club with this player | Jonathan Erlich | 20%
|
| Birthplace of a player who he beat in the 2016 Indian Wells finals | Podgorica | 20%
|
| Player who he beat to win his first title in Indian Wells Masters | Mardy Fish | 17%
|
| Player who beat him in his first match at the ATP tour level tournament | Filippo Volandri | 13%
|
| Player who he beat for the first victory on the ATP World Tour | Arnaud Clement | 7%
|
| Player who beat him in his first ATP Masters 1000 match | Fernando Gonzalez | 3%
|
| Player who he beat for the first Grand Slam victory | Robby Ginepri | 3%
|