World number one Andy Murray was knocked out of the Madrid Open as he lost in straight sets to Croat Borna Coric in the last 16.
Coric, 59th in the world rankings having secured his first ATP Tour title in Morocco last month, won 6-3 6-3.
The 20-year-old broke his British opponent three times in the opening set, and a further break in the second was enough to secure victory.
Coric will face either Grigor Dimitrov or Dominic Thiem in the quarter-finals.
Murray, 29, looked frustrated throughout as his testing clay-court season continued.
The Scot lost in the last 16 of the Monte Carlo Masters on his return from an elbow injury last month, and was then beaten by Thiem in the semi-finals of the Barcelona Open.
This was Coric’s second victory over Murray, having also beaten him at the Dubai Championships in 2015.
In a scrappy opening set, Coric broke to lead 3-2 but a couple of forehand errors allowed Murray to break straight back.
Murray, twice a winner in Madrid, then lost his serve once more, Coric comfortably held and Murray was unable to hold his serve to stay in the set.
His frustration boiled over in the eighth game of the second set as Coric won a long rally to break, before serving out the match.
Murray will next play in Rome, where he is the defending champion.
World number two Novak Djokovic reached the quarter-finals with a 6-4 7-5 defeat of Feliciano Lopez.
Defending champion Djokovic, who recently split with his coaching staff, had few problems against the 35-year-old Spaniard.
Belgium’s David Goffin is also through to the quarter-finals after beating Milos Raonic 6-4 6-2, while Kei Nishikori saw off David Ferrer 6-4 6-3.
Rafael Nadal plays Australian Nick Kyrgios later on Thursday.
Dimitrov, Coric advance on Wednesday
Alexander Zverev scored his first win on clay over a Top 10 player in the Emirates ATP Rankings, reaching the third round of the Mutua Madrid Open on Wednesday in a late-night thriller over seventh seed Marin Cilic 6-7(3), 6-3, 6-4.
The #NextGenATP German boosts his FedEx ATP Head2Head against Cilic to 3-1 and has won their past three matches.
He’ll now take on 11th seed Tomas Berdych for a place in the last eight after the Czech player defeated Robin Haase 7-6(5), 6-3. Zverev trails his FedEx ATP Head2Head with Berydch 1-4, but won their most recent meeting this past September in St. Petersburg.
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Cilic recovered from being a break down at 3-4 in the opening set and held the lead throughout the tie-break to take the early advantage. Zverev was forced to save six break points in his first two service games of the second set, but the momentum swung in his favour after clearing that hurdle. He only needed a single break of serve in each set to claim victory in two hours and 34 minutes.
Zverev has been a hot streak after prevailing on home soil last week in Munich to win his fourth ATP World Tour title and second of the season. He currently sits at No. 19 in the Emirates ATP Rankings, one spot off his career-high standing, but could surpass that with another big run this week.
Benoit Paire recorded the first major upset of the tournament on Court Manolo Santana, hanging tough to defeat third seed Stan Wawrinka 7-5, 4-6, 6-2.
The Frenchman improves his FedEx ATP Head2Head against Wawrinka to 3-7 and picks up his first win on clay against the former Roland Garros champion.
Next up for Paire is Pablo Cuevas, who won a marathon 5-7, 6-4, 6-4 match against Nicolas Mahut. The World No. 52 in the Emirates ATP Rankings leads his FedEx ATP Head2Head over Cuevas 3-0, including a win this March at the ATP World Tour Masters 1000 event in Miami.
Wawrinka was left to rue a series of missed opportunities in the first set. The Swiss star was up 4-2, 40/0, but let Paire back in with several errors and the Frenchman earned the break back with a volley winner. A forehand sent well long by Wawrinka gave Paire a 6-5 lead and the unseeded player comfortably wrapped up the set on serve in the next game.
A 15-minute rain delay pulled both men off the court at 2-2 in the second set. When they returned, it was Paire who stumbled out of the gate by double faulting to give Wawrinka a 3-2 lead. The third seed missed a chance to serve out the set at 5-3, but ripped a forehand return winner on set point in the next game to force a decider.
Wawrinka had momentum in his favour, but played a loose opening game in the third set to drop his serve. He then gave Paire an insurance break at 2-4 with a backhand error. Paire served out the match in the next game to advance in one hour and 48 minutes.
More: Djokovic Fights Hard For Almagro Win
In other second-round matches, 12th seed Grigor Dimitrov defeated Ivo Karlovic 6-3, 7-5 and will next play eighth seed Dominic Thiem. #NextGenATP Croatian Borna Coric, a lucky loser in the draw, moved past qualifier Pierre-Hugues Herbert 7-5, 6-4. The 20 year old is rewarded for his efforts with a round of 16 showdown against top seed Andy Murray.
Local favourite David Ferrer advanced without hitting a ball when 10th seed Jo-Wilfried Tsonga was forced to withdraw due to a shoulder injury.
View FedEx ATP Head2Head for the following match-ups Thursday at the Mutua Madrid Open & vote for who you think will win!
Nadal v Kyrgios | Djokovic v Lopez | Murray v Coric | Nishikori v Ferrer
View Thursday schedule
• Five of the Top 6 seeds are in third-round action at the Mutua Madrid Open on Thursday, including past champions Andy Murray, Novak Djokovic and Rafael Nadal. Murray meets #NextGenATP player Borna Coric, who could become the first lucky loser ever to reach the Madrid quarter-finals. Djokovic takes an 8-1 head-to-head record into his match with Madrid native Feliciano Lopez.
• Nadal, who leads all players with 30 wins in 2017 and four Madrid titles, faces No. 16 seed Nick Kyrgios for the third time. Their FedEx ATP Head2Head rivalry is even at one win each. Kyrgios hit 37 aces to stun then-No. 1 Nadal at 2014 Wimbledon as a 19-year-old wild card ranked 144th. But when they met again on the clay courts of Rome last May, Nadal rallied from a set down for the win.
• Spaniard David Ferrer seeks his 700th win for a second straight day after receiving a walkover from Jo-Wilfried Tsonga. Ferrer tries again against 2014 finalist Kei Nishikori, who defeated him at Caja Magica in 2014 and 2015. No. 11 seed Tomas Berdych is nearing a milestone of his own. The 2012 Madrid finalist, two wins shy of 600, meets #NextGenATP player Alexander Zverev.
• No. 5 seed Milos Raonic and No. 9 seed David Goffin will renew their rivalry, which includes the Canadian’s comeback from two sets down en route to the 2016 Wimbledon final. The 26-year-olds are both ranked in the Top 10 after reaching two finals each in 2017. They’ve come a long way from Australian Open qualifying in 2011, when then-No. 152 Raonic defeated then-No. 205 Goffin.
• Another all-seeded showdown pits No. 8 seed Dominic Thiem against No. 12 seed Grigor Dimitrov. Thiem and Dimitrov are among the four remaining players with one-handed backhands, joining Lopez and Pablo Cuevas. The unseeded Uruguayan meets Benoit Paire for a spot in his third ATP Masters 1000 quarter-final of 2017 (0 QFs in 28 prior ATP Masters 1000 appearances).
700-WINS CLUB (ALL PLAYERS)
Rank Player Wins
1 Jimmy Connors 1,256
2 Roger Federer* 1,099
3 Ivan Lendl 1,068
4 Guillermo Vilas 929
5 John McEnroe 877
6 Andre Agassi 870
7 Rafael Nadal* 836
8 Stefan Edberg 801
9 Ilie Nastase 780
10 Novak Djokovic* 766
11 Pete Sampras 762
12 Boris Becker 713
13 David Ferrer* 699
* Active Player
Second seeds Bob Bryan and Mike Bryan advanced to the Mutua Madrid Open quarter-finals with a 5-7, 6-2, 10-7 win over Fabrice Martin and Daniel Nestor on Wednesday. The Americans capitalised on both of their break point chances to reach the last eight in Madrid, where they will face Nick Kyrgios and Jack Sock.
Jamie Murray and Bruno Soares, the third seeds, defeated Juan Sebastian Cabal and Robert Farah 6-3, 7-6(4) in 82 minutes to set a quarter-final clash with sixth seeds Nicolas Mahut and Edouard Roger-Vasselin. The Frenchmen advanced with a 7-6(6), 7-6(3) win over Robin Haase and Albert Ramos-Vinolas.
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Ahead of the all-Madrid @ChampionsLeague showdown, @BrunoSoares82, @jamie_murray and @danielnestor ditched the rackets!#UCL #MMOPEN pic.twitter.com/6DfHLr7LaH— Tennis TV (@TennisTV) May 10, 2017
Lukasz Kubot and Marcelo Melo needed just 64 minutes to advance 6-3, 6-4 over Brian Baker and Nicholas Monroe. The fourth seeds await the winner of the match between seventh seeds Ivan Dodig/Marcel Granollers and Fabio Fognini/Treat Huey.
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Rafael Nadal’s winning streak now stands at 10 wins but will face it’s toughest task so far on Thursday…
Andy Murray continues his push for a third straight Madrid final on Thursday, taking on Borna Coric for a spot in the quarter…