#2 Lleyton Hewitt
Known for his rough-rider, never say die mentality, Lleyton Hewitt was one of a kind on the men's tour. Hewitt burst on to the scene at a very young age and caught the world's attention after beating Andre Agassi at the Next Generation Adelaide International in 1998.
In November 2001, Hewitt became the youngest male player to be ranked world number 1 at the age of 20 years and 8 months. He captured two Grand Slams, the US Open in 2001 and the Australian Open in 2002. He also won the World Tour Finals in 2001 and 2002. Injuries took a toll and Hewitt never really returned to his peak since.
Hewitt had a 9-18 H2H record against Federer and 4-7 record against Rafael Nadal. Notable losses against Federer include losing at the 2005 Wimbledon semifinals and 2004 quarterfinals.
#3 Juan Martin del Potro
At 6 feet 6 inches, Juan Martin del Potro possesses all the weapons you need as a tennis player to go down as one of the best ever. Unfortunately, a mixture of bad luck and consistent injuries has hampered the career of the Argentine.
One of the greatest servers the game has ever seen, del Potro has all the attributes to pick apart his opponents. His lone Grand Slam success came in the 2009 US Open where he beat five-time defending champion Roger Federer in five sets. It was to be the start of something special for the South American but that wasn't to the case.
Earlier that year, he lost the 2009 Australian Open quarterfinals to Federer in straight sets and succumed to defeat against the Swede in 2012 as well. He again lost in five sets against Federer at the Roland Garros earlier that year. In 2013, he lost the semifinals of the Wimbledon to Novak Djokovic and also lost the 2018 French Open semifinals to Rafa Nadal.
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