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Nadal upset by Canadian teenager in Montreal

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MONTREAL– Canadian teenager Denis Shapovalov upset top-seeded Rafael Nadal 3-6, 6-4, 7-6 (4) in the third round of the Rogers Cup on Thursday night.

The 18-year-old Shapovalov, from Richmond Hill, Ontario, advanced to a quarterfinal meeting Friday night with France’s Adrian Mannarino, who defeated Hyeon Chung of South Korea 6-3, 6-3.

“It’s what I dreamed of all my life growing up, playing guys like Rafa (Nadal), Roger (Federer), Andy (Murray),” Shapovalov said. “You know, my dream came true today.”

Shapovalov has taken major strides this week to reach his goal of cracking the world’s top 100 with wins over Rogerio Dutra Silva and 2009 U.S. Open champion Juan Martin Del Potro. He also halted Nadal’s bid to regain the No. 1 ranking, which the Spaniard could have achieved by reaching the semifinals.

Shapovalov battled back after Nadal cruised through the first set, then erased a 3-0 deficit in the tiebreaker for the biggest victory of his career.

Shapovalov became the youngest player to reach the tournament’s quarterfinals since Bjorn Borg in 1974. With hockey great Wayne Gretzky and Olympic swimming star Penny Oleksiak cheering for him from the seats, he also became the youngest quarterfinalist at a Masters Series tournament ever and is the youngest to beat a player ranked in the top two in the world since Nadal beat Federer in 2004 in Miami.

“He played well,” Nadal said. “He has a great potential.”

“I wish him the best. He has everything to become a great player. He played with the right determination in the important moments.”

Roger Federer overcame a weak first set to post a 4-6, 6-4, 6-2 victory over Spaniard David Ferrer in an earlier third-round match.

In Friday’s quarterfinals, the second-seeded Federer will face 12th-seeded Roberto Bautista Agut of Spain, who outlasted Frenchman Gael Monfils 4-6, 7-6 (5), 7-6 (2) on center court at Uniprix Stadium.

Unseeded Argentine Diego Schwartzman posted a strange win over American Jared Donaldson 0-6, 7-5, 7-5 to advance to a quarterfinal meeting with Robin Haase, the 52nd-ranked Dutchman who upset seventh-seeded Grigor Dimitrov of Bulgaria 7-6 (3), 4-6, 6-1.

Kevin Anderson of South Africa downed American Sam Querrey 6-4, 6-1 and will next play fourth-seeded Alexander Zverev, who ousted 16th-seeded Nick Kyrgios 6-4, 6-3.

Federer, who breezed past Canadian Peter Polansky in the second round on Wednesday, struggled in the opening set, spraying balls long, wide or into the net, but gradually rediscovered at least some of the form that has seen the 36-year-old Swiss earn two grand slam wins this year.

Federer is 17-0 in his career against the 35-year-old Ferrer, who was ranked third in the world in 2013 but is now at No.33.

Bautista Agut fought off a match point to force a tiebreaker, which the tired-looking Monfils opened with a double fault and never challenged again.

The unseeded Monfils played his third straight three-set match, including an upset win over fifth-seeded Kei Nishikori in the second round.

Schwartzman saved four match points to upset third-seeded Dominic Thiem in the second round. The win over Donaldson put him in a quarterfinal for the sixth time this year. Schwartzman’s only ATP win was on clay in Istanbul last year.

Donaldson, 20, was seeking a first career quarterfinal in a Masters Series tournament, where he is 0-13 in round of 16 matches.

Top-ranked Halep wins tough 3-setter in Miami

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KEY BISCAYNE, Fla. (AP) Top-ranked Simona Halep of Romania struggled to post a 3-6, 6-3, 7-5 second-round win over French lucky loser Oceane Dodin at the Miami Open on Thursday.

In the first career meeting between the players, Halep allowed the 98th-ranked Dodin to break her serve on six of seven opportunities she presented in the match, which lasted more than two hours.

Halep broke Dodin’s serve for the seventh time at 4-4 in the third set before closing it out.

Halep played in her third career Grand Slam final at the Australian Open in January, but has yet to secure a Grand Slam trophy.

Halep’s best Miami Open was reaching the 2015 semifinals.

Also Thursday, former No. 1 Angelique Kerber of Germany advanced to the third round with a 6-2, 6-2 win over Johanna Larsson of Sweden.

Kerber is 19-4 this year and has reached at least the quarterfinals of all five tournaments she’s played.

Kerber, the 2016 Australian Open and U.S. Open champion, won her first tournament since that U.S. Open at Sydney in January. She also reached the Australian Open semifinals.

Serena Williams loses in first round at Miami Open to Osaka

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KEY BISCAYNE, Fla. (AP) Serena Williams lost in the first round of the Miami Open on Wednesday, still rusty in her return from pregnancy and unable to overcome a tough draw against Naomi Osaka, who won 6-3, 6-2.

The 20-year-old Osaka, who earned her first career title Sunday at Indian Wells, showed no signs of letup and overpowered the erratic Williams. Osaka had the stronger serve, and in rallies wore down Williams working her from side to side.

The matchup worthy of a final came about because both players are unseeded. Osaka is ranked a career-best 22nd, while Williams’ ranking is 491st after her layoff of more than a year.

Another new mother and former No. 1, three-time Key Biscayne champion Victoria Azarenka, defeated Catherine Bellis 6-3, 6-0.

Williams has endured a first-round defeat only four other times, most recently at the 2012 French Open. The latest loss came at a tournament she has won a record eight times and considers her hometown event.

The match was the last for Williams at Key Biscayne, 90 miles south of her home in Palm Beach Gardens. The tournament is moving next year to the Miami Dolphins’ stadium, and Williams helped with the ceremonial groundbreaking Monday.

After her defeat, she left without speaking to the media.

Because of Williams’ ranking, she entered the draw as a wild card, and looked the part. She was a step slow to balls in the corners and often late with her swing, while she put barely half her first serves in play.

Osaka, who has both American and Japanese citizenship and lives in Fort Lauderdale, was playing her idol for the first time but didn’t seem a bit fazed. She improved to 14-4 this year.

Things may get tougher for her in the second round, when she’ll face No. 4-seeded Elina Svitolina.

More AP tennis coverage: https://apnews.com/tag/apf-Tennis