#4. Nicolas Massu
He may not have been a very popular player of his generation but Nicolas Massu will always be remembered for his performances at the 2004 Athens Olympics where he won the gold medal in both the singles and doubles tournaments, becoming the only male player to do so in the same Olympics.
At the same time, his two gold medals have been Chile’s only gold medals in their Olympic history.He couldn’t have the same amount of success in Grand Slams as he never made it past the quarter-finals in any of the Grand Slams. The closest he came to reaching the quarter-finals of a Grand Slam was during the 2005 US Open where he reached the fourth round and was two sets to one up against former French Open runner-up Guillermo Coria before the Argentine came back to win the match.
Massu’s best performances at the other majors were reaching the second round of the Australian Open in 2005, third round of the French Open in 2004 and 2006, and reaching the third round of Wimbledon in 2001. Not a very convincing Grand Slam CV for a player who had entered the Top 10.
