Cameron Norrie has been knocked out of the Monte Carlo Masters, losing 6-4 2-6 6-4 to Spain's Albert Ramos-Vinolas in the second round.
It was the first time the pair had met on clay since Ramos-Vinolas overcame the British number one in three sets at the Estoril Open last year.
Ramos-Vinolas ensured it would be four wins in a row on clay against the world No. 10 with a three-set victory in two hours and 31 minutes.
Norrie through to second round with win over Andujar, Miyazaki and Burrage out
The 34-year-old Spaniard will play 11th seed Hubert Hurkacz in the third round after he beat ATP Santiago champion Pedro Martinez 6-3 4-6 6-4.
Norrie, who received a bye in the first round as the tournament's seventh seed, recovered from a set and a break down to force a decider as Ramos-Vinolas appeared to be struggling with an abdominal injury.
But Ramos-Vinolas fought back to record the eighth victory of his career against a player in the world's top 10.
“We always have good matches and he’s in the top 10 so for me today it’s a great win,” Ramos-Vinolas said afterwards.
“I started off well and was 2-0 up in the second set but tennis is like this.
"I lost seven [games] in a row but somehow I start to play good and I’m happy to be in the next round."
Norrie rescued a break point in the first game of the match, but was broken in the seventh. The 26-year-old could not convert his only break point of the set as Ramos-Vinolas served it out.
Momentum was with Ramos-Vinolas and he broke in the opening game of the second set and went into a 2-0 lead. But Norrie fought back and reeled off six games in a row to force a decider.
Ramos-Vinolas took a painkiller for his abdominal injury before the third set and it seemed to do the trick as the Spaniard secured the decisive break of serve in the seventh game before converting his second match point to move into the next round.
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EVANS LOSES TO GOFFIN
There was more bad news for British tennis fans as Dan Evans lost in straight sets to David Goffin 7-6(3) 6-2.
Evans, who reached the Monte Carlo Masters semi-finals last year after beating Goffin in the quarter-finals in three sets, saved five break points in the opening set before the Belgian triumphed in the tie-break.
The world No. 47 broke the Evans serve three times in the second to seal a comfortable victory in two hours and three minutes.
Goffin will play Novak Djokovic's conqueror Alejandro Davidovich Fokina next.
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