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No. 3 seed Stefanos Tsitsipas has become the highest men’s seed to fall at the Tokyo Olympics, getting knocked out in the third round by Ugo Humbert, 2-6, 7-6 (4), 6-2.

Humbert’s win over the No. 4-ranked Greek is the biggest win of his career.

After falling behind by a double break and eventually dropping the first set after just 32 minutes, a win seemed like a longshot for the No. 28-ranked Humbert. But he stayed on serve with Tsitsipas throughout the second set until the tie-break, where he opened up a 6-3 lead, closing it out two points later—and Tsitsipas’ troubles only grew from there as he fell to the court on set point, clutching his leg, which he then received treatment on.

Tsitsipas managed a hold for 1-0 in the third set but from there it was all Humbert—the Frenchman won five games in a row to build a 5-1 lead. Tsitsipas held to close the gap to 5-2 and even had four break points in the next game to get one break back, but Humbert hung tough, sneaking out a seven-deuce game with an ace on his fourth match point.

Humbert, who won the biggest title of his career at the ATP 500 in Halle two weeks before Wimbledon, scored his fifth career Top 10 win. He got his first two in 2020, beating No. 5 Danill Medvedev on clay in Hamburg and No. 6 Tsitsipas on indoor hard in Paris, and his next two came on grass in Halle, against No. 6 Alexander Zverev and No. 7 Andrey Rublev.

The Frenchman is now 2-0 in his head-to-head against Tsitsipas.

Tsitsipas, who reached his first Grand Slam final at Roland Garros this year, fell to the court on set point in the second set and was then treated for a leg injury.

Tsitsipas, who reached his first Grand Slam final at Roland Garros this year, fell to the court on set point in the second set and was then treated for a leg injury.

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Despite the loss, Tsitsipas still had a notable run in Tokyo. By winning his first-round match against Philipp Kohlschreiber, he became the first Greek man to win a singles match at the Olympics since Augustos Zerlandis in 1924—then, he beat Frances Tiafoe in the second round, avenging a first-round loss to the American at Wimbledon a few weeks ago.

Awaiting the No. 14-seeded Humbert in the quarterfinals will be No. 12-seeded Russian Karen Khachanov, who also pulled off a surprise in his third-round match earlier in the day, beating No. 8 seed Diego Schwartzman in a streaky three-setter, 6-1, 2-6, 6-1.

Humbert and Khachanov will be playing each other for the first time.