World number one Andy Murray lost 6-3 6-3 to unseeded Borna Coric in the Madrid Open third round on Thursday as his hard start to the claycourt season continued, while Rafa Nadal and Novak Djokovic eased into the quarter-finals.
Coric also won his first ATP title, on clay, this year, beating the likes of Albert Ramos-Vinolas, Diego Schwartzman and Philipp Kohlschreiber en route to success in Marrakech.
World No. 59 Coric, who won his first ATP title last month in the Grand Prix Hassan II in Marrakech, took the second break point to serve out for the match, sending last year's finalist and two-time Madrid victor Murray packing.
He will play the quarterfinal against Dominic Thiem of Austria, who won a thriller against Grigor Dimitrov of Bulgaria 4-6, 6-4, 7-6 (9).
"Even though I played really badly, my attitude has been very positive", Nadal said. He then earned two break points in the third game but was unable to take advantage.
Number one seed Andy Murray moved into the third round of the Mutua Madrid Open tennis tournament on Tuesday following comfortable straight sets 6-4, 6-3 win over Rumanian wildcard Marius Copil.
The 14-time Grand Slam champion had a slice of fortune as a let cord and a Kyrgios double fault handed him the two breaks he needed to take the first set.
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It was the 11th straight win for Nadal, and his tour-leading 30th victory for the year.
"I played a lot better", said Nadal, who struggled in a three-set win over Fabio Fognini on Wednesday. He withdrew from Barcelona last month because of a right wrist injury.
In another match, David Goffin of Belgium defeated Canadian Milos Raonic 6-4, 6-2 to reach the quarters.
Uruguay's Pablo Cuevas recovered from losing the second set 6-0 to beat Benoit Paire and will meet Germany's Alexander Zverev, a 6-4 6-4 victor over Tomas Berdych.
On the women's side, third-seeded Simona Halep of Romania reached the semifinals by beating Coco Vandeweghe of the US 6-1, 6-1. "I don't know. But I try to see every day". "It's always tough to play with someone who has a big serve".
Svetlana Kuznetsova ended Eugenie Bouchard's impressive run to the quarters in convincing fashion 6-4, 6-0.
Since returning from an elbow injury last month, Murray has also crashed out of the Monte Carlo Masters at the last-16 stage and the semi-finals of the Barcelona Open, where he lost to Thiem.
Bouchard ousted Maria Sharapova in the second round.