Eight-time Wimbledon champion Roger Federer lost 6-3, 7-6 (4), 6-0 to 14th-seeded Hubert Hurkacz of Poland in the quarterfinals at the All England Club on Wednesday.
Federer turns 40 next month and never was able to summon the serving and shot-making that have carried him to 20 Grand Slam titles overall.
That is tied with Rafael Nadal for the most by a man in tennis history.
Hurkacz is a 24-year-old from Poland who had not made it past the third round at any major tournament until this one.
Earlier, Denis Shapovalov reached his first Grand Slam semifinal by edging Karen Khachanov in five sets at Wimbledon.
The 10th-seeded Shapovalov pulled out the 6-4, 3-6, 5-7, 6-1, 6-4 victory over the 25th-seeded Khachanov in nearly 3 1/2 hours at No. 1 Court. Shapovalov is a 22-year-old from Canada who won the 2016 Wimbledon boys' title.
He compiled nearly twice as many winners as Khachanov, 59-31. That total included 17 aces for Shapovalov, which helped lessen the importance of his 10 double-faults.
The last break came at 4-all in the fifth set. Shapovalov converted his fourth break chance in that game when Khachanov sent a forehand long.
Shapovalov will face No. 1 Novak Djokovic on Friday for a berth in the final.