Carlos Alcaraz secured his fifth ATP Tour title and second Masters 1000 crown by cruising past defending champion Alexander Zverev 6-3 6-1 at the Madrid Open.

Alcaraz became the first player to ever defeat Rafael Nadal and Novak Djokovic in consecutive matches en route to the final in the Spanish capital, while Zverev edged out Stefanos Tsitsipas to make the showpiece.

Zverev, a two-time winner in Madrid in 2018 and 2021, boasted a 2-0 head-to-head record over Alcaraz on the ATP Tour heading into the clash on Sunday, but it was the 19-year-old who seized the early initiative.

Alcaraz struck first with a break to go 4-2 up after a dipping backhand evaded the reach of Zverev, who could not muster a response as the Spaniard served out a dominant first set.

The teenager continued in commanding fashion in the second set, delivering a deft drop shot to break Zverev, who missed two straightforward volleys and produced a double fault to fall 4-1 down.

World number three Zverev managed to save three match points, but a double fault then handed Alcaraz victory in just 62 minutes, becoming the youngest five-time tour winner since Nadal won seven titles by the same age in 2004-05.

Alcaraz leads the way for wins in the 2022 season as his 10th straight triumph – and seventh consecutive victory over top-10 ranked players – takes him to 28 for the campaign, one more than Tsitsipas.

Alcaraz is also the second-youngest player to win two ATP Masters 1000 titles, after triumphing in Miami in March, and will rise to second in the Race to Turin as he seeks his debut at the prestigious end-of-season event in November.

Alexander Zverev avenged his Monte Carlo semi-final loss to Stefanos Tsitsipas, booking his place at the Madrid Open final with a 6-4 3-6 6-2 win on Saturday.

Zverev was dominant on serve, giving up only two break points for the match with a 73 per cent first-serve rate, while winning 40 of a total 48 points on his first serve.

The German will now aim to defend his title in Sunday's final when he faces Carlos Alcaraz, who defeated world number one Novak Djokovic earlier on Saturday.

The second seed will be seeking his sixth ATP 1000 title, with Sunday's final against the home favourite to be his 10th at that level.

"I'm just extremely happy to be in the final here," Zverev said post-match. "I know it's going to be an extremely tough match tomorrow but I hope I can manage to play my best and give myself a chance.

"It's going to be his [Alcaraz] court for the next 15 years probably. It has been Rafa's [Nadal] court for the past 15 years and it's going to be his court for the next 15 years.

"I just hope I can give him some trouble and I hope I can manage to win tomorrow."

Tsitsipas was similarly strong on his first serve but had a much lower rate at only 56 per cent for the match. Zverev simply had more looks at his opponent's second serve, winning 15 points compared to Tsitsipas' eight, but with each holding a 44 per cent success rate.

The defending champion at Caja Magica capitalised when it mattered, though, claiming the opening three games in the deciding set to set up the eventual win.

Rafael Nadal saved four match points before seeing off David Goffin 6-3 5-7 7-6 (11-9) to book his place in the Madrid Open quarter-finals.

A five-time champion in the Spanish capital, Nadal is looking to match Novak Djokovic's career record of 37 ATP Masters 1000 titles this week.

Returning to action for the first time since losing to Taylor Fritz in the Indian Wells final, after which he discovered he had a stress fracture of a rib, Nadal was taken all the way by Goffin.

Indeed, the Belgian qualifier won four straight games from 5-3 down in the second set to force a decider, but he saw four opportunities to advance to the quarter-finals go begging.

Nadal subsequently prevailed to reach his 99th Masters 1000 quarter-final, setting up a last-eight showdown with teenage compatriot Carlos Alcaraz.

Birthday boy Alcaraz, who turned 19 on Thursday, celebrated with a hard-earned 6-4 6-7 (4-7) 6-3 victory over Britain's Cameron Norrie.

Defending champion Alexander Zverev reached his fifth successive quarter-final at this event after beating Lorenzo Musetti, who retired with a thigh injury shortly after losing the opening set, at 6-3 1-0 down.

Next up for Zverev is Felix Auger-Aliassime, the Rotterdam Open champion, who is targeting a first clay-court Masters 1000 semi-final. Auger-Aliassime won 90 per cent of points on first serve in a commanding 6-1 6-2 victory over Jannik Sinner.

Stefanos Tsitsipas also produced a strong-serving display in his 6-3 6-4 triumph over Grigor Dimitrov. Last season’s French Open runner-up hit 10 aces along the way.

The fourth seed set up a showdown with Andrey Rublev, who had eight aces as he overcame Dan Evans 7-6 (9-7) 7-5.

Meanwhile, Hubert Hurkacz will play Djokovic in the last eight after hitting 16 aces in his 7-5 6-3 win over Dusan Lajovic. Djokovic's much-anticipated clash with Andy Murray was called off, with the Briton unwell, handing his Serbian rival a walkover.

Novak Djokovic set up a last-16 clash with Andy Murray at the Madrid Open, impressing in a straight-sets victory over Gael Monfils while Murray overcame Denis Shapovalov.

The 20-time grand slam champion eased to a 6-3 6-2 win in the Spanish capital, assuring him of a record-extending 369th week at the top of the ATP world rankings and teeing up a mouth-watering contest with one of his greatest rivals.

The Serb hailed his victory as representing his best performance of 2022, saying he was pleased with his progress after falling to a final defeat against Andrey Rublev on home soil in last month's Belgrade Open.

"[It was] probably the best match of the year so far for me," Djokovic told Tennis TV after the win. "I haven't played many matches and am still finding my groove.

"But [it's] a very good win against a very tricky opponent. I had a week, 10 days to get ready for this match, and for this tournament I have done everything I possibly can to build my fitness and also improve on all aspects of the game, on the court. 

"I'm really glad that it paid off, because I felt good on the court. It's the right process, and it's the right direction."

Djokovic will face Murray for the 37th time, and the first time since 2017's Qatar Open, after the three-time grand slam winner rolled back the years to overcome Shapovalov 6-1 3-6 6-2 in an absorbing two-hour contest later on Tuesday.

The duo are one of only two male pairs to have met in each of the four grand slam finals (along with Djokovic and Rafael Nadal), while Djokovic holds a 25-11 lead across their previous meetings and has won both of their two encounters at the Madrid Open, one of which was their first-ever meeting in 2006.

Elsewhere in the draw, it was a day of few shocks in Spain as seeds Rublev and Carlos Alcaraz ensured their own progress to the last 16.

Rublev recovered from a poor first-set showing to down Great Britain's Jack Draper 2-6 6-4 7-5, while home favourite Alcaraz remained on course for a potential meeting with compatriot Nadal after earning a 6-3 7-5 victory over Nikoloz Basilashvili.

Finally, 2014 US Open champion Marin Cilic beat Albert Ramos-Vinolas 6-3 3-6 6-4 in a competitive first-round affair to set up Wednesday's enticing last-32 clash with world number three Alexander Zverev.

Alexander Zverev is out of the BMW Open after a shock straight-sets defeat to Holger Rune in the last 16 in Munich.

The world number three and top seed had no answer to an impressive performance from Rune, with the young Dane ultimately easing to a 6-3 6-2 victory on Wednesday.

Rune set the tempo early on, moving Zverev around the court with plenty of drop shots and heading into a 4-2 lead, before saving two break points on his way to clinching the first set.

An early break in the second then seemed to give the 18-year-old the confidence to see out his first career victory against a top 10 opponent.

"It was a difficult match from the beginning," said Rune on-court after the win. "He's in the top three in the world and has been playing some unbelievable tennis, especially in the past year winning so many big titles.

"I have a lot of respect for him, and I obviously didn't expect to win in two sets, and with a score like this. But it was a really hard match, we played a lot of rallies and I'm really happy about my performance today."

Rune will play Emil Ruusuvuori in the quarter-finals after the Finn beat Maxime Cressy 6-3 6-3.

Elsewhere, fourth seed Nikoloz Basilashvili came from behind to overcome Ilya Ivashka 3-6 6-2 6-4, and will face Miomir Kecmanovic in the last eight after the seventh seed beat Daniel Altmaier 6-2 6-4.

There were also three round of 32 matches on Wednesday, with eighth seed Botic van de Zandschulp, Egor Gerasimov and Alejandro Tabilo all through to the last 16 in Munich.

Over at the Estoril Open, Alejandro Davidovich Fokina will play Frances Tiafoe in the quarter-finals after both advanced in Portugal.

Fourth seed Davidovich Fokina beat fellow Spaniard Bernabe Zapata Miralles 6-3 7-6 (7-5) while fifth seed Tiafoe got the better of Nuno Borges 7-6 (7-4) 4-6 6-0.

Fernando Verdasco is also through after a 6-2 6-3 win against Pablo Cuevas, and he will play fellow Spaniard and sixth seed Albert Ramos-Vinolas, who came from a set down against Kwon Soon-woo, 5-7 6-1 6-2.

Alexander Zverev will play Holger Rune and Casper Ruud is set to face Alex Molcan in the round of 16 at the BMW Open.

Zverev and Ruud – the number one and two seeds respectively – received byes in the round of 32, with Danish wildcard Rune defeating Jiri Lehecka 7-6 (7-4) 6-3 to advance in Munich on Monday, and Molcan beating fellow Slovakian Norbert Gombos 6-1 3-6 7-6 (9-7).

Teenager Rune had won his opening match in four of his past five tour-level events ahead of the tournament and extended that run with relative ease.

There were no problems for seventh seed Miomir Kecmanovic as he overcame Max Hans Rehberg in straight sets, 6-2 6-3, and he will face Daniel Altmaier in the last 16 after he beat his German compatriot Philipp Kohlschreiber 7-6 (7-5) 3-6 6-1.

Emil Ruusuvuori is also through after beating Japanese opponent Yoshihito Nishioka 7-6 (7-5) 7-5, and the Finn will now go up against the winner of Dan Evans and Maxime Cressy.

At the Estoril Open, Alejandro Davidovich Fokina, who reached the final in Monte Carlo earlier this month, will face fellow Spaniard Bernabe Zapata Miralles next after he overcame Federico Coria 6-4 6-3.

Fifth seed Frances Tiafoe secured a victory against Dusan Lajovic, with the American coming from a set down to win 2-6 7-5 6-0, and up next for him is Nuno Borges in the last 16.

Borges advanced after opponent Pablo Andujar retired hurt in the second set, although the Portuguese was already a set and 3-0 up at the time, while Soonwoo Kwon eased past Benoit Paire in straight sets.

Stefanos Tsitsipas remains on course for a second consecutive Monte Carlo Masters title after recording a straight-sets semi-final win over Alexander Zverev.

The third seed, who defeated Andrey Rublev to clinch the title in Monaco last year, produced a scintillating performance to beat the world number three 6-4 6-2 in Saturday's last-four encounter.

Tsitsipas will face world number 46 Alejandro Davidovich Fokina in Sunday's final, and the Greek said he will need to perform at an even higher level to defeat the 22-year-old, whose incredible run continued with a three-set win over Grigor Dimitrov in the final four.

"It was good," Tstispas told Amazon Prime Video of his semi-final win. "I don't know whether the long match [his three-set quarter-final win over Diego Schwartzman on Friday] gave me some rhythm, but I was able to play good tennis today. I'm happy with the level I was able to execute, and I came up with some good ideas on the court.

"I'm looking forward to the next one, I have a difficult opponent tomorrow, so I need to be ready and to take the best out of this one and move on.

"It's going to take a little bit more [to beat Davidovich Fokina], he's in a good rhythm. I've played him before, and he's a difficult opponent, I'm going to be as ready as possible, he's definitely improved and I'm going to have to produce the best tennis I can."

Davidovich Fokina, who has made headlines by eliminating Novak Djokovic and Indian Wells Masters champion Taylor Fritz during a thrilling run in the municipality, beat Dimitrov 6-4 6-7 (2-7) 6-3 earlier on Saturday, reaching his first ATP Tour final.

The unseeded Spaniard needed two hours and 43 minutes to wrap up his semi-final contest, and revealed that a bathroom break allowed him to reset his mind and clinch a hard-fought victory after he failed to serve out the second set at 5-4 up.

"I am so happy to be in the final, it's a dream come true to try to have the title," he said after the win.

"When I was a kid, I was dreaming about this day and it's come true, I'm so happy.

"In the second set I had my chances, I was so tight. But I went to the bathroom [after the second set] and I said to myself 'I want this'. Now I am in the final, I will enjoy, I have all the power with me."

Reigning Monte Carlo Masters champion Stefanos Tsitsipas will have to overcome Alexander Zverev if he is to have the chance to defend his title.

Zverev, who is ranked third in the world - two places higher than Tsitsipas - fought back to defeat Jannik Sinner 5-7 6-3 7-6 (7-5) in his quarter-final match, denying his opponent another top-five seed scalp following his prior win over Andrey Rublev.

"It means a lot, definitely, especially [with] how this year has been going so far for me," said Zverev after a gruelling three hours on court.

"I've lost long matches like that, so I’m happy I won this one."

Tsitsipas also orchestrated a superb turnaround against Diego Schwartzman, prevailing 6-2 6-7 (3-7) 6-4.

The Greek had looked set for a last-eight exit at four games down in the final set, only to stage a dramatic comeback to keep his hopes of a first title since last May's Lyon Open alive.

"There was a moment in the match where I felt what I was doing wasn't working," Tsitsipas said.

"He had a massive lead and momentum in what he was trying to do. I just tried to stay in the match as much as I could and that worked out very well.

"I wasn't expecting much at that point being a double break down, so I relaxed at that point."

Schwartzman meanwhile will rue his inability to put the tie to bed, having already reached two ATP finals this year.

Grigor Dimitrov and Alejandro Davidovich Fokina will face off in the other semi-final.

Bulgarian Dimitrov beat off Hubert Hurkacz in another final-set tie-break, winning 6-4 3-6 7-6 (7-2).

Fokina, who eliminated Novak Djokovic in the second round, turned over Indian Wells champion Taylor Fritz in another comeback result, triumphing 2-6 6-4 6-3.

Alexander Zverev and Stefanos Tsitsipas progressed to the quarter-finals of the Monte Carlo Masters with straight sets wins on Thursday, remaining on course for a final meeting.

Last year's runner-up Andrey Rublev, however, missed out on a last-eight spot after falling to a three-set defeat against Jannik Sinner.

World number three Zverev overcame Spain's Pablo Carreno Busta 6-2 7-5 to progress in Monaco, where he is seeking to win the sixth ATP 1000 title of his career.

"For the second clay-court match of the season, I can't complain too much," the 24-year-old second seed said on court after sealing the victory.

"Yes, I lost focus a little bit in the second set, but at the end of the day, he's somebody that can really play. I'm happy with a two-set win."

Tsitsipas (3) remains in contention for a second consecutive title in the principality after defeating Laslo Dere 7-5 7-6 (7-1) and will face off against 12th seed Diego Schwartzman for a semi-final spot after the Argentine defeated Lorenzo Musetti in a hard-fought three-set encounter.

There will be no repeat of 2021's final between Tsitsipas and Rublev, however, after the Russian fell to a thrilling 5-7 6-1 6-3 loss to ninth seed Sinner in the day's final contest.

The other seed to fall victim to a shock in the last 16 was world number seven Casper Ruud, losing 6-3 7-5 to Grigor Dimitrov, who will face Poland's Hubert Hurkacz in the last eight. 

Finally, Novak Djokovic's conqueror Alejandro Davidovich Fokina cruised past David Goffin 6-4 6-1 to set up a quarter-final tie with the United States' Taylor Fritz, who bested compatriot Sebastian Korda – with whom he played doubles with in Monte Carlo – in straight sets.

In light of recent high-profile misconduct, the ATP has warned players of harsher punishments for on-court behaviour in an internal note, as it also reviews its framework for stopping repeat offenders.

Nick Kyrgios was fined for audible obscenities and hurling his racquet onto the ground after his defeat to Rafael Nadal in Indian Wells – almost hitting a ballkid - while Alexander Zverev was thrown out of the Mexican Open in February after smashing his racquet repeatedly against the umpire's chair.

Jenson Brooksby also came under fire at the Miami Masters, throwing his racquet and hitting a ballkid in his win over Federico Coria, with Coria also motioning during the match that the consequent point penalty was not sufficient.

The recent spate of on-court outbursts has prompted the ATP to act.

"Effective immediately and as we head into the clay court swing, the ATP officiating team has been directed to take a stricter stance in judging violations of the Code of Conduct," ATP Tour chief Andrea Gaudenzi wrote in a circular to the players.

"Additionally, we are also undertaking a review of the Code, as well as the disciplinary processes, to ensure that it provides appropriate and up-to-date penalties for serious violations and repeat offenders."

Kyrgios was also fined after his loss to Jannik Sinner in Miami for criticising the umpire and smashing his racquet, and although Zverev was handed an eight-week suspension for his outburst in Acapulco, the ATP appears determined to nullify future misconduct.

While Gaudenzi, the Italian former top 20 player, understood the human elements to players competing under extreme pressure, he asserted the game itself should be taken into consideration.

"The first three months of the season have seen an unusual frequency of high-profile incidents involving unsportsmanlike conduct," Gaudenzi wrote.

"These incidents shine a bad light on our sport. This conduct affects everyone, and sends the wrong message to our fans, especially young fans."

Casper Ruud set up a semi-final with Francisco Cerundolo at the Miami Masters after he defeated Alexander Zverev 6-3 1-6 6-3 on Wednesday.

Ruud's heavy topspin game gave Zverev problems initially, contributing to a 94 per cent success rate from points on his first serve, while Zverev struggled to find rhythm on serve at 58 per cent.

Saving two break points in the opening game of the second seemed to spark Zverev into life, but Ruud was able to regroup and continue dominating from the baseline in the third to comfortably see his way through.

"It was great to get that break early on [in the third set] and I was able to keep it all the way out," Ruud said post-match. "I was serving well. I can thank my serving for the win today."

The Norweigian world number eight lost his first three ATP 1000 quarter-finals on hard court, but played with confidence on the back of a 75 per cent first-serve rate.

He will face Cerundolo, who also advanced into the semi-finals on Wednesday, after Jannik Sinner was forced to retire due to foot blisters. The Argentine was leading 4-1 in the first set after 23 minutes when Sinner called the match.

The world number 103 held a 0-2 record on hard courts prior to this week, but has now made his first ATP 1000 semi-final in as many attempts after progressing past Tallon Griekspoor, Reilly Opelka, Gael Monfils and Frances Tiafoe.

Cerundolo has enjoyed a strong start to 2022, with respective quarter-final and semi-final appearances on clay in Buenos Aires and Rio de Janeiro.

The winner of the upcoming semi-final will make their first ATP 1000 final appearance, while Ruud was able to beat Zverev at third time of asking, losing the opening two games head-to-head.

Emerging Spanish star Carlos Alcaraz continued his rise with a 7-5 6-3 upset of third seed Stefanos Tsitsipas to reach the Miami Masters quarter-finals on Tuesday.

The 18-year-old, who reached last year's US Open final eight after beating Tsitsipas in the third round, proved too good again for the Greek in one hour and 50 minutes.

Alcaraz reached last week's Indian Wells semi-finals and is now 15-2 on the season, with the win setting up a clash with Serbian Miomir Kecmanovic who upset last week's Indian Wells champion Taylor Fritz 3-6 6-1 6-4.

Tsitsipas broke the Spaniard in the sixth game and led 5-2 before Alcaraz reeled off seven straight games to sensationally take the first set.

Alcaraz surged ahead in the second set, with his defence and speed leaving Tsitsipas short on answers.

The Spaniard, who saved seven of eight break points throughout the match, converted his fourth match point for victory.

"It was really, really tough. He was playing unbelievable," Alcaraz said after the match. "All I can say is I fought until the last ball in the first set [to] come back."

Ninth seed Jannik Sinner won 7-6 (7-3) 6-3 over enigmatic Australian Nick Kyrgios, who had a furious outburst directed at umpire Carlos Bernardes.

The Australian was heard to label Bernardes "an absolute clown" and continued to berate the umpire late in the first set, leading to a code violation and two penalties.

Kyrgios completely lost his cool, demanding to speak to a tournament official before smashing his racquet early in the second set, leading to a game penalty as well.

Sinner will next take on Argentine Francisco Cerundolo after he defeated 28th seed Francis Tiafoe lost 6-7 (2-7) 7-6 (7-3) 6-2.

Top seed Daniil Medvedev made light work of Jenson Brooksby 7-5 6-1 to set up a quarter-final showdown with reigning champion Hubert Hurkacz who won 7-6 (7-3) 6-2 over Lloyd Harris. Medvedev will return to the top of the ATP rankings if he wins their quarter-final.

Second seed Alexander Zverev got past Thanasi Kokkinakis 6-4 6-4 and will meet sixth seed Casper Ruud in the last eight, after the Norwegian won 6-3 6-4 over Briton Cameron Norrie.

Jannik Sinner saved multiple match points for the second straight match on Sunday, advancing to the last-16 at the Miami Masters.

After saving three in his opening match against Emil Ruusuvuoiri, the 20-year-old Italian denied Pablo Carreno Busta five times to eventually win 5-7 7-5 7-5.

A Miami finalist in 2021, the Italian was 5-4 down in the second set before winning 11 consecutive points to force a third frame.

Down a break before breaking-to-love in the third, Sinner was fearless with his ground strokes with the game on the line, moving to 5-0 in deciding sets for 2022.

He will face Nick Kyrgios, who continued his strong start to the year with a 6-2 6-4 win over Fabio Fognini.

Taking only 61 minutes to advance after defeating world number seven Andrey Rublev in straight sets in his opening match, Kyrgios hit 24 winners and only lost eight points on serve.

The Australian wildcard and Sinner were supposed to meet at Indian Wells earlier this year, but the latter had to withdraw due to illness.

Fellow unseeded Australian Thanasi Kokkinakis advanced past Denis Kudla, while Francisco Cerundolo upset Gael Monfils.

In the late result on Sunday, Alexander Zverev was a comfortable 6-2 6-2 winner over Mackenzie McDonald.

The German second seed put McDonald under immediate pressure with his return of service, winning 13 of 22 points on the American's second serve.

Meanwhile, Cameron Norrie and Casper Ruud saw their way through in straight sets.

Fifth seed Andrey Rublev has been eliminated from the Miami Open in the second round in straight sets by wild card world number 102 Nick Kyrgios on Friday.

The enigmatic Australian triumphed 6-3 6-0 in 52 minutes to clinch a third round clash with Italian Fabio Fognini, who won in three sets against Japanese Taro Daniel.

The victory marks Kyrgios' third win over a top 10 opponent in the past two tournaments, having topped both Casper Ruud and Jannik Sinner at Indian Wells earlier this month.

Rublev had won titles in Marseille and Dubai earlier this season but was not allowed to settle by Kyrgios who sent down 10-5 aces and had a first serve percentage of 80 per cent.

"I know that he's a player who relies on a bit of rhythm, so I just tried to keep the points short and sharp, just play aggressive," Kyrgios said after the match.

"I'm just happy with my performance, whether it's 7-6 in the third or something like this, I'm just happy to get through."

Second seed Alexander Zverev was made to work for victory against Croatian Borna Coric, winning 6-4 3-6 6-3 in two hours and one minute.

The win marks the 2018 Miami Open runner-up's first triumph at the event since that run to the final.

Sixth seed Ruud eased past Henri Laaksonen 6-1 6-2, while ninth seed Sinner defeated Emil Ruusuvuori 6-4 3-6 7-6 (10-8) in two hours and 40 minutes.

Several seeds were beaten included 13th seed Diego Schwartzman who went down 4-6 7-6 (7-3) 6-4 to Thanasi Kokkinakis. Seeds Lorenzo Sonego, Grigor Dimitrov, Reilly Opelka and John Isner also exited.

Gael Monfils defeated Oscar Otte 7-6 (11-9) 6-1, Pablo Carreno Busta won 6-3 6-2 over David Goffin and 10th seed Cameron Norrie won 7-6 (7-5) 6-4 over Jack Draper.

Third seed Alexander Zverev has been knocked out of the Indian Wells Masters by Tommy Paul in his first game since his expulsion from last month's Mexican Open for unsportsmanlike conduct.

Unseeded American Paul triumphed over the German 6-2 4-6 7-6 (7-2) in two hours and 17 minutes, rallying back from a break down in the final set.

Paul hit less winners, 26-21 to Zverev but made less unforced errors 25-19, while his serve and volley game was a key feature.

"I played a really high level today," Paul said during his on-court post-game interview. "The last time I played him, I played well, I put pressure on him so I knew how i wanted to play so I came out and executed him well.

"I played well when it came down to the breaker, so I'm pretty happy with my performance."

Zverev had not played since being expelled in Acapulco after a stunning outburst where he struck his racquet on the umpire chair several times after a doubles defeat.

Ninth seed Felix Auger-Aliassime was a major casualty, going down to Dutchman Botic van de Zandschulp 7-6 (7-4) 6-7 (4-7) 6-3 in three hours and 15 minutes.

The Canadian had 36-27 winners but was let down by 43-26 unforced errors, along with converting only two of his 10 break points.

Van de Zandschulp had failed to take three match points in the second set but showed composure to finish the job in the third.

Wild card Andy Murray was also eliminated in the second round, blowing three set points in the first set before going down to 31st seed Alexander Bublik 7-6 (11-9) 6-3 in two hours and one minute.

Last year's Wimbledon runner-up and Italian sixth seed Matteo Berrettini needed more than two hours to get past world number 86 Holger Rune 6-3 4-6 6-4.

Seventh seed Andrey Rublev defeated Dominik Koepfer 7-5 6-4 to extend his win streak to 10 matches, while 11th seed Hubert Hurkacz beat Oscar Otte 6-3 3-6 6-3.

Other seeds to be eliminated were 22nd seed Aslan Karatsev who went down 7-6 (7-5) 6-4 to American Steve Johnson, while 24th seed Marin Cilic lost 6-7 (7-9) 6-3 7-6 (8-6) to Miomir Kecmanovic.