They often referred to themselves as the "Spice Girls of Tennis".
However, Anna left this "dream-team" and ended her professional tennis career prematurely at the age of 21 due to serious back and spinal problems.
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Kournikova, who would often top the charts as the most searched celebrity on search engine Google during her playing career, was perhaps more in the limelight for her relationships.
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She was linked to NHL ice hockey players like Pavel Bure and Sergei Fedorov – with the latter claiming to be married to her.
Anna Kournikova (right) was linked to NHL ice hockey player Sergei Fedorov (centre).