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Britain's Jack Draper succumbed to a last-16 defeat by Alejandro Davidovich Fokina in an entertaining match at the Monte Carlo Masters.
The 23-year-old twice came back from a break down in the deciding set but could not find a consistent level, losing 6-3 6-7 (6-8) 6-4 to the Spaniard.
Indian Wells champion Draper had cruised to victory in his first clay-court match of the year but looked out-of-sorts at times against Davidovich Fokina.
The new world number six made 46 unforced errors, recorded 10 costly double faults and converted just four of his 16 break opportunities.
Clay has not previously been Draper's favourite surface but, after receiving a first-round bye, his performance against American Marcos Giron in round two showed promise.
The British number one was not at his best in the opening set against Davidovich Fokina, berating himself throughout with cries of "wake up" and come on" in an attempt to increase his energy.
However, that form dragged into the second set, with Draper hitting three double faults on his way to being broken in the opening game.
Trailing by a set and a break, Draper's fortunes changed when he hit an ace to hold serve after saving two break points, raising his arms in relief before playing a fine return game to break back for 3-3.
He saved a match point on the way to forcing a tie-break and ensured a deciding set with a stunning cross-court forehand winner.
The pair traded breaks in a third set of shifting momentum but Draper struggled to take his chances, converting just two of his nine break points while 42nd-ranked Davidovich Fokina converted all three of his opportunities.
Second seed Carlos Alcaraz takes on German Daniel Altmaier later on Thursday, with Daniil Medvedev and Matteo Berrettini also in action.
Meanwhile, British doubles pair Neal Skupski and Joe Salisbury lost their last-16 match 6-3 6-3 to compatriot Henry Patten and his Finnish partner Harri Heliovaara.