Court level view of World No.4 Stefanos Tsitsipas playing against former World No.8 Karen Khachanov on grass before Wimbledon 2019.

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Tsitsipas has a career-high ranking of No. 4 in the world, making him the highest-ranked Greek player in history. In 2021, he reached the finals of the French Open, falling to Novak Djokovic in 5 sets after leading by 2 sets. He has also reached the semi-finals twice at the Australian Open.

Khachanov achieved his career-high singles ranking of world No. 8 on 15 July 2019, after reaching the quarterfinals of the 2019 French Open. He also claimed his first ATP Masters 1000 title at the 2018 Rolex Paris Masters by defeating World No. 9 John Isner in the third round (saving two match points), World No. 5 Alexander Zverev in the Quarterfinals, World No. 8 Dominic Thiem in the Semi-finals and World No. 1 Novak Djokovic in the Finals. The then World No. 18 Khachanov was the lowest-ranked player to claim a Masters 1000 title since Ivan Ljubicic won the 2010 Indian Wells Masters.

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