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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.
There was joy for some seeded players though as Australian Alex de Minaur and France’s Gael Monfils went through after victories over Jaume Munar and Stan Wawrinka respectively.
Ninth seed De Minaur, who reached the quarter-finals at the French Open in May, beat Spain’s Munar 6-2 6-2 7-5 .
Gael Monfils, back at Wimbledon for the first time since 2021, saw off Swiss three-time Grand Slam champion Wawrinka 7-6 (7-5) 6-4 7-6 (7-3).
“It was a veteran battle,” Monfils said.
“Stan is someone I look up to. It’s always a privilege to play him. Today I won, but I know the next one it could be him.”
Bulgarian 10th seed Grigor Dimitrov is next up for Monfils after he came from two sets down to beat China’s Shang Juncheng 5-7 6-7 (4-7) 6-4 6-2 6-4.
Late on Court One, fourth seed Alexander Zverev defeated American Marcos Giron 6-2 6-1 6-4. The German will face Britain’s Cameron Norrie in the third round.
Elsewhere, American 13th seed Taylor Fritz and Danish 15th seed Holger Rune both needed four sets to get past Frenchman Arthur Rinderknech and Brazilian Thiago Seyboth Wild respectively.
American 14th seed Ben Shelton came through a five-set encounter to beat South African Lloyd Harris, while Italian 25th seed Lorenzo Musetti went the distance in victory against compatriot Luciano Darderi.