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5. Ana Ivanovic
Now retired, Ivanovic held the No. 1 position in the world back in 2008. She has won 15 WTA Tour singles titles including a French Open and a Grand Slam singles title. During her hey day, Ivanovic made more than $15 million in prize money as a result she became one of the highest paid tennis players. Over the years, Ivanovic has earned several accolades like Top 100 Greatest Players Ever and Time’s “30 Legends of Women’s Tennis: The Past, Present, and Future” where she was ranked in number one position.