WIMBLEDON, England – Rafael Nadal of Spain ran out of comebacks at Wimbledon, losing to a brash, big-serving, between-the-legs-hitting 19-year-old who might be a future star.

Russian Maria Sharapova, somehow, seemed on the verge of a turnaround despite a flurry of unforced errors, saving six match points before finally losing on the seventh with — what else? — a missed shot.

And in perhaps the most striking sight of a memorable day of departures by past Wimbledon champions, American Serena Williams couldn’t get the ball over the net in a doubles match, stopping after three games because of what was termed a viral illness.

The most noteworthy winner Tuesday was 144th-ranked Nick Kyrgios, an Australian who used 37 aces and a have-no-fear approach to beat Nadal 7-6 (7-5), 5-7, 7-6 (7-5), 6-3 for a quarterfinal berth.

“I was in a bit of a zone out there,” said the 6-foot-4 Kyrgios, the lowest-ranked player to beat the No. 1 man at any Grand Slam tournament in 22 years.

“You’ve got to believe you can win the match from the very start, and I definitely thought that. I’m playing some unbelievable tennis on the grass.”

That’s for sure.

Playing in his fifth major tournament, Kyrgios is the first man to reach the quarterfinals in his Wimbledon debut in 10 years. He is also the first teen to defeat the top-ranked man at a Grand Slam event since Nadal was 19 when he beat Roger Federer at the 2005 French Open.

“We keep saying, ‘Who’s the next guy?’ And I think we may have found him,” seven-time major champion John McEnroe said on the BBC broadcast.

Nadal, the Wimbledon champion in 2008 and 2010, lost to No. 135 Steve Darcis in the first round here last year and bowed to No. 100 Lukas Rosol in the second round in 2012.

“The thing is, (on) this surface, when you have an opponent that decides to serve and to hit every ball very strong, you are in trouble,” Nadal said.

Kyrgios joked about reading that his mother said she didn’t think he could beat Nadal.

“It actually made me a bit angry,” he said. “I’ll just text her a smiley face.”

Fifth-seeded Sharapova lost to No. 9 Angelique Kerber of Germany 7-6 (7-4), 4-6, 6-4. Sharapova made 49 unforced errors, 38 more than Kerber.

“She’s never really a player that gives you a lot of mistakes or lots of errors,” Sharapova said of Kerber. “You really have to win the match against her.

“She’s a great anticipator of the ball, one of the best.”

Williams, eliminated by Alize Cornet of France in the third round of singles Saturday, was in obvious distress before she and sister Venus faced Kristina Barrois and Stefanie Voegele in doubles.

Serena, the top-ranked woman in the world, pushed volleys into the net from a couple of feet away and whiffed on some practice strokes. After she was examined for about 10 minutes on the sideline by medical staff, including a check of her blood pressure, the match began. It lasted less than a set.

“I am heartbroken I’m not able to continue in the tournament,” Serena said in a statement. “I thought I could rally this morning because I really wanted to compete, but this bug just got the best of me.”