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#2 Miloslav Mecir
The former player from Slovakia won the Olympics singles Gold in 1988 and even reached the finals of two Grand Slams(US Open in 1986 and Australian Open in 1989) but failed to win either of them, losing both to Ivan Lendl.
However, he did win the year-ending Championships in 1987, defeating John McEnroe in the final. He won a total of 11 titles in his singles career and reached a career-high ranking of no. 4 in the world in February 1988.
He retired from the sport in the year 1990.
#1 Elena Dementieva
Elena Dementieva consistently performed well at the top stage and was constantly beating top players but failed to win a single Grand Slam title. Just like Mecir, Dementieva too won the Olympics singles Gold. She achieved this feat in 2008, defeating Dinara Safina in the Gold medal encounter in Beijing.
She reached the final of the 2004 French Open and US Open and cracked the semis of the Grand Slams on 7 other occasions. She won a total of 16 titles in her singles career and reached a career-high ranking of no. 3 in 2009. She retired from the sport in 2010 after the year-ending Championships.
