Second seed Stefanos Tsitsipas was bundled out of the Miami Open in straight sets during Tuesday's fourth round by 2022 US Open semi-finalist Karen Khachanov.
The Russian 14th seed prevailed 7-6 (7-4) 6-4 over Tsitsipas in one hour and 34 minutes, powering 25 winners and making only nine unforced errors, compared to the Greek's 14.
Khachanov's triumph ended a winless 0-6 head-to-head record against Tsitsipas, while it also snapped his own 23-match losing streak against top-10 opponents.
The Russian, who also made this year's Australian Open semi-finals, has qualified for four of his six tour-level events this year.
Khachanov will take on 25th seed Francisco Cerundolo in the quarter-finals, with the Argentinian fighting back to get past Lorenzo Sonego 3-6 6-3 6-2 in just over two hours.
Defending champion and top seed Carlos Alcaraz had less trouble against Tommy Paul, cruising into the quarter-finals with a 6-4 6-4 victory.
Alcaraz won the winners' count 24-9, setting up a quarter-final clash with ninth seed Taylor Fritz, as the Spanish 19-year-old chases a rare Sunshine Double, having won last week's Indian Wells Open.
Fritz progressed after getting past seventh seed Holger Rune 6-3 6-4 in 86 minutes, sending down eight aces and 22 winners for the match.
Fourth seed Daniil Medvedev played late into the evening after a lengthy rain delay in Miami, but made light work of Quinten Halys 6-4 6-2, triumphing just past 1:30am local time.
Medvedev, who is into his third straight Miami quarter-final, will face American qualifier Christopher Eubanks in the last eight after he got past Frenchman Adrian Mannarino 7-6 (7-2) 7-6 (7-5) in another rain-delayed contest.
Italian 10th seed Jannik Sinner knocked off sixth seed Andrey Rublev 6-2 6-4, advancing to face Emil Ruusuvuori after he beat Botic van de Zandschulp 4-6 6-4 7-5.
Alcaraz sends Spain into Davis Cup last eight
Carlos Alcaraz has led Spain to the quarter-finals of the Davis Cup Finals after a straight-sets win over Ugo Humbert.
The 21-year-old needed just one hour and 21 minutes to cruise through with a 6-3 6-3 victory, hitting 21 winners to his opponent's 14 as he backed up Roberto Bautista's win earlier on.
Bautista had to come from behind to edge past Arthur Fils, beating him 2-6 7-5 6-3, and converting 40% of his break points, bettering the Frenchman's 27%.
Spain are through in Group B, but elsewhere in Group D, US Open semi-finalist Jack Draper's return was unable to inspire Great Britain to victory.
Dan Evans was beaten by Tomas Martin Etcheverry earlier on Friday before Draper's first match since New York ended in a straight-sets 7-6 (7-4) 7-5 defeat to Francisco Cerundolo.
Despite making fewer unforced errors than the Argentinian (23 to 39), the British number one struggled to find an edge, though Evans and Neal Skupski claimed a consolation win in the doubles to make it 2-1.
They sit second in the group, missing the chance to qualify for the last eight, and now needing a win against Canada, who have been in fine form so far.
Auger-Aliassime and Shapovalov sweep aside Finland at Davis Cup
Felix Auger-Aliassime and Denis Shapovalov moved Canada to the brink of qualification in the Davis Cup Finals group stage, comfortably dispatching Finland in Manchester.
Shapovalov needed just an hour and 13 minutes to beat Eero Vasa 7-6 (7-2) 6-2, backing up his win against Argentine Francisco Cerundolo on Tuesday.
The Canadian served five aces to his opponents' three, producing three love games in the final set to get his nation off to a flying start.
Auger-Aliassime followed up Shapovalov's victory with another straight sets win, this time over Otto Virtanen, emerging a 6-2 6-3 victor.
The world number 21 was dominant on serve throughout his 73-minute triumph, saving all three break points he faced and winning 86% of his first-serve points.
Auger-Aliassime and Shapovalov then prevailed in the doubles against Harri Heliovaara and Virtanen in another straight sets win, putting them top of Group D without dropping a set against their opponents.
Nadal confirms Laver Cup withdrawal to help Team Europe 'deliver the win'
Rafael Nadal confirmed he will not participate in next month's Laver Cup, believing there are "other players who can help the team deliver the win" for Team Europe.
Nadal last played at the Paris Olympics alongside Carlos Alcaraz in the men's doubles, with the Spanish duo knocked out at the quarter-final stage at Roland Garros.
The 38-year-old also competed in the singles but was hampered by a thigh problem in Paris and suffered a second-round loss to eventual gold medallist Novak Djokovic.
Nadal participated in the inaugural edition of the Laver Cup seven years ago, defeating Jack Sock to help Team Europe claim a 15-9 victory.
It is yet to be confirmed who will replace the 22-time grand slam champion in Berlin next month as captain Bjorn Borg now goes in search of adding to his star-studded line-up.
Alexander Zverev, Alcaraz, Daniil Medvedev, Casper Ruud and Stefanos Tsitsipas have already been confirmed as the participants to face Team World in Berlin.
Nadal posted a statement on social media, saying that he was making the decision for the benefit of the team.
“I’m really disappointed to share that I won’t be able to compete at the Laver Cup in Berlin next week," Nadal said.
"This is a team competition and to really support Team Europe, I need to do what’s best for them and at this moment there are other players who can help the team deliver the win.
"I have so many great, emotional memories from playing in the Laver Cup, and I was really looking forward to being with my teammates and with Bjorn in his final year as Captain.
"I wish Team Europe the very best of luck and will be cheering them on from afar.”
The news will accelerate speculation that retirement could be imminent for the Spaniard, who was unsure of his future following his exit from the Olympic Games.
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