Raven Klaasen and Rajeev Ram advanced to their second ATP World Tour Masters 1000 semi-final of the season on Friday, beating Frenchmen Fabrice Martin and Edouard Roger-Vasselin 5-7, 7-5, 10-8 at the Coupe Rogers in Montreal.

The South African and American pairing hit 10 aces and claimed 87 per cent of their first-serve points to move into the last four. They also reached the semi-finals of the BNP Paribas Open in Indian Wells, where they won their first Masters 1000 title (d. Kubot/Melo).

The sixth seeds will next face Indian Rohan Bopanna and Croatian Ivan Dodig, who beat another French team in Gael Monfils and Benoit Paire 6-2, 7-5. Bopanna/Dodig saved three of four break points to advance in 74 minutes.

Fifth seeds Pierre-Hugues Herbert and Nicolas Mahut escaped two tight sets against fourth seeds Bob Bryan and Mike Bryan 7-6(5), 7-6(11) to reach their third Masters 1000 semi-final of the season. The Frenchmen fell in the semi-finals at the Monte-Carlo Rolex Masters (l. to Lopez/Lopez) and won the Internazionali BNL d’Italia title in Rome (d. Dodig/Granollers).

They will face top seeds Henri Kontinen and John Peers or Oliver Marach and Mate Pavic in the last four.

Robin Haase dared to dream and delivered on Friday when he booked a spot in the Coupe Rogers semi-finals, his first at an ATP World Tour Masters 1000 tournament.

Haase extended his perfect record to 5-0 against Argentinean Diego Schwartzman in a hard-fought 4-6, 6-3, 6-3 quarter-final victory over two hours and four minutes.

The Dutchman, competing at his 35th tournament at the Masters 1000 level, will next face Swiss second seed and two-time former champion Roger Federer or No. 12 seed Roberto Bautista Agut of Spain. Haase’s previous best result had been one quarter-final exit at the 2012 Monte-Carlo Rolex Masters (l. to Djokovic).

Schwartzman played aggressively from the outset, pouncing on any half chance in the opener, but lapses in concentration coupled with tiredness – after three straight three-setters – let Haase back into the match. While Haase tightened up and let slip a 3-0 lead in the decider, from 3-3 he lost only six points for his 24th match win of the year.

“The week for me was very good, but I am now disappointed as I don’t think I played well in the second and third sets,” Schwartzman told ATPWorldTour.com. “I didn’t play too well from the baseline, but Haase served better to get back into the match.”

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World No. 6 Marin Cilic announced on Friday that he has been forced to withdraw from the Western & Southern Open in Cincinnati, where he is the defending champion, due to an abductor injury.

“I was really eager to play in Cincinnati, where I won my first-career ATP World Tour Masters 1000 singles title last year and where I’ve had some of the best performances during my career, but I still don’t feel at 100 per cent to compete at the top level and to defend my title there,” said Cilic.

“I had already started with my preparation and the progress is going well, but there isn’t enough time for me to prepare for Cincinnati and to be completely ready to play there. I feel very confident that I will be back in action very soon.”

The 28-year-old Cilic suffered the injury last month at Wimbledon, where he lost to Roger Federer in the final on 16 July.

Two unseeded opponents – a World No. 143, the other No. 42 in the Emirates ATP Rankings – were all that stood between Rafael Nadal and a return to No. 1 in Montreal by Thursday night. Defeat to the unheralded NextGenATP wild card Denis Shapovalov before a raucous Coupe Rogers crowd, however, means the Spaniard will now turn his sights to Cincinnati.

There the 30 year old will enter a two-horse race at the Western & Southern Open, where he and Roger Federer will bid to take over No. 1 in the Emirates ATP Rankings. The 3-6, 6-4, 7-6(4) loss to the 18 year old Canadian was difficult to take as a subsequent victory over the No. 42-ranked Frenchman Adrian Mannarino in the quarter-finals would have returned Nadal to top spot for the first time in more than three years.

“It probably is the worst lose of the year, without a doubt, for me,” Nadal said. “He played well. I played really bad. When this kind of thing happens, the only thing you can do is wish the opponent the best.

“It is probably my worst loss of the year because I lost against a player with a lower ranking. At the same time, because of the opportunity I had here to come back to No. 1. Always tough, but the draw was not that impossible after all the matches that were happening. So it was an important mistake from me.” 

In a gruelling deciding set in the battle of the two lefties, Nadal failed to convert on six break points. He later relinquished a 3-0 lead in the deciding tie-break. It marked his fourth straight deciding-set tie-break defeat.

“He played well on the breakpoints. He hit some lines. One with 15-30, he hit the second serve ace wide. Then a good return for me, forehand winner down the line, not easy,” Nadal said. “[Despite] all these kind of things, I made too many mistakes on important points.”

Shapovalov became the youngest player to beat at Top 2 opponent (in a completed match) since a 17-year-old Nadal beat top-ranked Federer in the 2004 ATP Masters 1000 Miami third round. Nadal, for one, was not surprised his teenage opponent’s nerves did not crack.

“He has nothing to lose. It is win-win for him,” Nadal said. “If he lost playing a good match, it was good for him. If he lost in straight sets, already he played a good tournament. If he won, he’s amazing. Just well done for him. It’s a great story.”

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#NextGenATP Canadian Denis Shapovalov delivered the performance of his career on Thursday evening, stunning World No. 2 Rafael Nadal 3-6, 6-4, 7-6(4) in front of an electric Court Central crowd at the Coupe Rogers in Montreal.

Shapovalov becomes the youngest quarter-finalist at an ATP World Tour Masters 1000 tournament. He’s also the second-youngest player to beat Nadal (Coric, 2014 Basel).

“It’s so tough. A lot of the times he just hits a shot that’s way too good. I was managing to get a lot back when I could. But, you know, he’s honestly the best player I’ve ever played in my life,” Shapovalov said.

“You could tell why he’s won so many Grand Slams. His ball was just so heavy. He’s such a warrior out there. So it’s honestly, like a dream come true for me to beat a player like that.”

Watch Thursday highlights featuring Federer v Ferrer and Nadal v Shapovalov

For the Spaniard, a return to No. 1 in the Emirates ATP Rankings will have to wait. Nadal would have returned to No. 1 for the first time since June 2014 if he had reached the semi-finals in Montreal.

Andy Murray will remain at No. 1 for another week but at the Western & Southern Open in Cincinnati next week, Nadal and Roger Federer will battle for the top spot.

Shapovalov, No. 143 in the Emirates ATP Rankings, is projected to reach a new career high and crack the Top 100 at No. 100. On Friday, he will look to continue his dream run at his home Masters 1000 tournament when he faces Frenchman Adrian Mannarino, who dismissed #NextGenATP Korean Hyeon Chung 6-3, 6-3 to reach his first Masters 1000 quarter-final in his 31^st attempt.

But this much is clear so far: Shapovalov brings an entirely different level of tennis to Court Central. The 18 year old has now knocked off three top ATP World Tour players on that court during the past two years: Nick Kyrgios last year, Juan Martin del Potro earlier this week and Nadal became his latest upset victim in their marathon two-hour and 46-minute battle.

“It’s a very fast pace right now. It’s a lot to take in, obviously. But to be honest, I’m very thankful that I’m in this position,” Shapovalov said. “If I didn’t save those four match points in the first round [against Dutra Silva], there wouldn’t even be a chance to play Juan Martin or Rafa. I’m very thankful for that.”

The teenager was under no illusions as to the calibre of opponent across the net from him. 

With “The Great One” Wayne Gretzky and his wife in attendance, Shapovalov was ready from the start for another high-octane match in the Canadian metropolis. He fought to 3-3 with Nadal in the opening set, but the Spaniard sprinted through the remainder of the opener and looked as if he would need only two sets.

Shapovalov, though, came out strong in the second set, and had two chances to go up 5-1. But Nadal fought back and pushed the second set to 4-4 before Shapovalov recovered to even the third-round match.

On his first set point, the Canadian mishit a return that Nadal lifted long, and Shapovalov raised his arms to roars from his thousands of fans.

The Canadian had success exchanging forehands with Nadal and was fearless with his shot selection, taking every cheer as encouragement. For the match, the Canadian finished with 49 winners to 41 unforced errors. He delivered nine aces to only two from Nadal.

Shapovalov also dealt an effective 1-2 punch while returning, pushing Nadal to one corner before striking a one-handed backhand or forehand up the line.

But Nadal, a 30-time Masters 1000 titlist, dug in for the decider, as did Shapovalov. Serving at 1-1, the 18 year old erased three break points and held during a 14-minute and 30-second game, showing the Spaniard he was not going away in the final set. For the match, Shapovalov erased nine of 11 break points.

In the tie-break, it again looked as if Nadal would finally pull away. He jumped out to a 3/0 lead. But this time it was Shapovalov’s turn to fight back, and he won seven of the tie-break’s final eight points to earn the biggest win of his life. Fittingly, he blasted a forehand winner on his first match point.

After the ball sped past Nadal, Shapovalov tossed his racquet and fell to the court, covering his eyes in disbelief. The crowd’s cheers soaked their new home favourite and, after he shook hands with Nadal, Shapovalov finished his celebration by saying thanks. He kissed the court and blew kisses to the crowd.

“I don’t know if a lot of players fold or if he just outplays them at the end,” Shapovalov said. “I was down 3-0 in the tie-break. I did a good job to regroup. I knew I had to win both the points off my serve. Yeah, then he gave me a double [fault] to tie it up.

“I just tried to stay calm, tried to play every point, go for my shots. At the end of the day I really tried to keep playing my game and stick to my tactics.” 

DID YOU KNOW?

With his win over No. 2-ranked Rafael Nadal, Denis Shapovalov…

• At 18 years, 3 months, is the youngest quarter-finalist in ATP Masters 1000 history (since 1990)

• Is the youngest quarter-finalist in Coupe Rogers tournament history since Bjorn Borg (18 years, 2 months) in 1974

• Came in this week ranked No. 143 and he could break the Top 100 in the Emirates ATP Rankings next week (depending on other results)…At the moment he is projected to be No. 100. If he beats Adrian Mannarino to reach the SFs, he is projected to jump to around No. 66.

• Is the lowest-ranked player to beat a Top 2 opponent since No. 144 Kyrgios beat No. 1 Nadal in 2014 Wimbledon fourth round.

• Is the lowest-ranked player Nadal has lost to since No. 144 Kyrgios (Nadal ranked No. 1 at the time) in 2014 Wimbledon fourth round.

• Is the youngest player to beat a Top 2 opponent since Filip Krajinovic, 18, beat No. 2 Djokovic (by retirement) in 2010 Belgrade QF. The previous instance in a COMPLETED MATCH was Nadal, 17, beating No. 1 Federer in 2004 ATP Masters 1000 Miami 3R

• Is the lowest-ranked ATP Masters 1000 quarter-finalist since No. 239 Ivo Karlovic at 2011 Indian wells and lowest-ranked Canada quarter-finalist since No. 144 Harel Levy in 2000

The crowd support playing in a French-speaking part of the world is doing the French doubles players no harm at this week’s Coupe Rogers with three duos advancing to the Coupe Rogers quarter-finals in Montreal. The all-French pairing of Fabrice Martin and Edouard Roger-Vasselin pulled off the biggest upset of the day when they defeated No. 2 seeds Lukasz Kubot and Marcelo Melo 6-4, 6-2.

Not to be outdone, Gael Monfils and Benoit Paire pulled off an upset of their own when they took down the No. 3 seeds Jamie Murray and Bruno Soares. The Frenchman prevailed 7-6(4), 6-7(5), 10-5 in one hour and 51 minutes.

There was guaranteed to be at least one all-French pairing into the quarter-finals as fifth seeds Pierre-Hugues Herbert and Nicolas Mahut took to the court against Lucas Pouille and Jo-Wilfried Tsonga. Herbert and Mahut booked their place in the quarter-finals with a 6-1, 6-7(5), 10-3 result over their compatriots.

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