Eleventh seed Stefanos Tsitsipas and seventh seed Hubert Hurkacz were both knocked out in the second round on a difficult day for the favourites at Wimbledon.
Two-time Grand Slam finalist Tsitsipas was beaten 7-6 (8-6) 7-6 (12-10) 3-6 6-3 by Finnish world number 88 Emil Ruusuvuori.
Hurkacz retired while defending match point against Frenchman Arthur Fils.
Three other seeds were beaten on day four, including Briton’s Jack Draper, while second seed Novak Djokovic survived a scare against British wildcard Jacob Fearnley.
By beating Tsitsipas, Ruusuvuori – who is into the third round at Wimbledon for the first time – recorded his first Grand Slam win over a top 20 player in 2024.
Poland’s Hurkacz went down with an injury while leading 8-7 in a fourth set tie-break but opted to retire after losing the next two points.
It meant Frenchman Fils became the youngest player to defeat a top-10 opponent in the men’s singles at SW19 since Nick Kyrgios beat Rafael Nadal in 2014.
Fils, 20, advanced 7-6 (7-2) 6-4 2-6 6-6 (9-8) and will face Russian Roman Safiullin next after he beat Tomas Machac of the Czech Republic in four sets.
There were further seeded causalities on day four with Russian former quarter-finalist Karen Khachanov beaten 4-6 6-3 3-6 6-3 6-4 by French qualifier Quentin Halys.
Argentina’s Tomas Martin Etcheverry, seeded 30th, also came out on the wrong side of a five-set battle against Australian Alexei Popyrin, losing 3-6 6-4 4-6 6-4 6-3.
Sixth seed Andrey Rublev remains the highest ranked player to exit the men’s singles after his first round loss on day two.
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