Marin Cilic, the last remaining Grand Slam winner in his half of the draw, crashed out of the US Open on Friday.
Croatian fifth seed Cilic, the 2014 US Open champion who missed six weeks since Wimbledon with an adductor strain, was eliminated by Argentine 29th seed Diego Schwartzman 4-6, 7-5, 7-5, 6-4.
The South American, now 2-13 against top-10 opponents, plays his first Slam last-16 match against the later winner between French 16th seed Lucas Pouille and Kazak qualifier Mikhail Kukushkin in a draw half without a top-10 player.
Cilic was broken serving for the first set only to break back to win it. Schwartzman failed on his first chance serving for the set in each of the last three sets before making the most of a second chance, denying two break points in a tense final game.
"The last game was terrible," Schwartzman said. "In my mind I can't play. I'm trying to improve my tennis. I'll try to be more quiet in the end of the next match when I finish."
SHAPOVALOV BECOMES YOUNGEST MAN IN LAST-16 SINCE 1989
Canadian teen Denis Shapovalov became the youngest man since 1989 into the US Open last 16 when Britain's Kyle Edmund retired with a neck injury with the former leading 3-6, 6-3, 6-3, 1-0.
Not since 17-year-old Michael Chang 28 years ago had a younger player cracked the fourth round in New York. And no qualifier had reached the last 16 since Gilles Muller in 2008.
"It's never great to win this way. Hopefully it's nothing too serious," said Shapovalov. "It's very unfortunate but at the same time I'm happy to be in the fourth round."
Shapovalov will play for a quarter-final berth against Spanish 12th seed Pablo Carreno Busta, who ousted French qualifier Nicolas Mahut 6-3, 6-4, 6-3.
CARRENO BUSTA CRUISES PAST MAHUT
Spaniard Pablo Carreno Busta hit 32 winners to beat Frenchman Nicholas Mahut 6-3, 6-4, 6-3 and seal a fourth-round spot. The 26-year-old has progressed past the third round of the U.S. Open for the first time, as he targets a first grand slam title.
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