The five-time champion Venus Williams was beaten by Dutch Kiki Bertens in the third round, being the second person from last year's finalists to lose before the fourth round.
There was no great escape for Venus Williams on Friday as the five-time champion became the latest top-10 seed to perish at Wimbledon after she was beaten 6-2 6-7(5) 8-6 in a pulsating third-round match by Dutchwoman Kiki Bertens.
The American, at 38 the oldest woman in the draw, had to recover from a set down in her first two matches but her days of living dangerously were ended by a opponent who simply would not give up.
"I still can't really believe it. It was such a tough match and such a big fight, and I'm really happy that I won this one," a breathless Bertens said moments after emerging victorious in the two hour, 40 minute thriller.
A poker-faced Williams summed up the experience as: "Just ran out of time in the end. You have to win the last point, and I didn't succeed in that today."
In fact, even in the first set Williams kept failing to win the points that mattered. She was 40-0 up on serve in the third game but a successful Hawkeye challenge combined with a lunging mis-hit winner from Bertens allowed the Dutchwoman to streak 3-0 ahead.
However, the precision serve that had gone AWOL during the first set – with the ninth seed holding serve only once – was back on target for Williams as she produced some exquisite volley winners to snap up the second set when Bertens smacked a forehand long.
But all the effort she put into forcing a decider despite being two points from defeat at 4-5 down in the second set came to nothing as Bertens played the match of her life to reach the second week at the All England Club for the first time in her career.
Bertens had come agonisingly close to toppling Williams in Miami this year, when she had held three match points, and on Friday it was clear she had learned from that near miss.
When match point number one disappeared with a stretched volley winner from Williams on Court One - Bertens kept believing.
When match point number two vanished with a wild backhand error, Bertens did not lose faith.
When match point three ended with the American netting a tired backhand into the net, Bertens dropped to her knees in triumph.
"I played her in Miami and had a few match points there and I lost so of course that was going through my mind, but I told myself to keep going," said 20th seed Bertens.
"I told myself, 'you're in the Wimbledon third round, never reached the fourth round so you have nothing to lose so go for your shots'."
Friday's result meant both last year's finalists have lost before the fourth round, with Williams following 2017 champion Garbine Muguruza out of the tournament.
Her demise also continued the horror show for women's seeds at Wimbledon as only two of the top 10 – world number one Simona Halep and number seven Karolina Pliskova – are still in the tournament. It is the worst showing by the women's seeds in the professional era.
Advancing into the fourth round
Ninth-seeded John Isner of the US reached Wimbledon's fourth round for the first time, beating 98th-ranked Radu Albot of Moldova 6-3, 6-3, 6-4.
Isner will face No 31 Stefanos Tsitsipas for a quarterfinal berth.
Tsitsipas became the first Greek man to reach the fourth round of a Grand Slam tournament in the 50-year professional era.
The 19-year-old Tsitsipas beat Thomas Fabbiano of Italy 6-2, 6-1, 6-4 at Wimbledon in 91 minutes.
Serena Williams ran her Wimbledon winning streak to 17 matches and also moved into the fourth round with a 7-5, 7-6 (2) victory over 62nd-ranked Kristina Mladenovic of France, thanks in part to 13 aces.
The 36-year-old American will face 120th-ranked qualifier Evgeniya Rodina of Russia in the fourth round on Monday.
Gael Monfils advanced to the fourth round at Wimbledon for the first time after knocking out last year's semifinalist Sam Querrey 5-7, 6-4, 6-4, 6-2.
Monfils will next face eighth-seeded Kevin Anderson.
Camila Giorgi of Italy advanced to the fourth round at Wimbledon after saving a match point while beating Katerina Siniakova of the Czech Republic 3-6, 7-6 (6) 6-2.
She will next face 35th-ranked Ekaterina Makarova, who overcame another Czech, Lucie Safarova, 4-6, 6-4, 6-1.