Alex de Minaur's French Open preparations have suffered another blow, beaten by qualifier Aslan Karatsev at the Madrid Open.
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The Australian world No.19 went down 6-3 4-6 6-4 to the Russian, who is ranked 101 places below him, but is a former top-20 player.
Monday's two-hour 16-minute contest seemed to be swinging de Minaur's way when he broke at 5-4 to win the second set. But Karatsev broke in the fifth game of the decider and despite forcing deuces in both the tenth and 12th games the 'Demon' could not find a way to break back.
De Minaur had only won once at each of his previous two tournaments on clay, in Barcelona and Monte Carlo, and this early exit is another setback to his Roland Garros preparations.
The 24-year-old could have set up a last-16 match against Daniil Medvedev, who came from a break down twice in the final set to beat fellow Russian Alexander Shevchenko a 4-6 6-1 7-5.
"He played well. He's young, so I'm sure he's going to (move) up the rankings, especially if he plays like in this tournament," Medvedev said of the 96th-ranked Shevchenko, who was making his main-draw debut in Madrid after coming through qualifying.
The 22-year-old Shevchenko, who appeared to struggle with cramps toward the end of the match, took a 5-1 lead in the first set but went down 5-0 in the second. He then led 2-0 and 4-2 in the decisive set.
Francis Tiafoe's poor start to the European claycourt season continued with a 6-1 7-6 (7-2) defeat to world No.67 Pedro Cachin. The American world No.11 lost in the opening round in Barcelona last month.
But Stefanos Tsitsipas and Taylor Fritz are through, with wins over Sebastian Baez and Cristian Garin respectively.
Fritz will face Zhizhen Zhang next after the Chinese eliminated British No.1 Cameron Norrie.
Norrie, seeded 11th in the Spanish capital, looked to be cruising when he won four games in a row to take the first set and the second looked to be following a similar pattern.
However, the world No.99 hit back to record a 2-6 7-6 (7-2) 7-6 (7-2) victory.
Third seed Tsitsipas earned a 7-5 3-6 6-3 win over the 31st-ranked Argentine to secure his spot in the last 16.
"I had to bring the best out of my game," Tsitsipas said.
"Of course he's someone that covers and runs around the court pretty well. He definitely utilised that pretty well against me, being able to navigate himself throughout the entire court with ease, just gliding through the court like a cheetah."
Tsitsipas, seeking his first title of the season, improved to 8-2 on clay. The Greek was a finalist in the Australian Open and last week in Barcelona. He also was a finalist in Madrid in 2019, and a semi-finalist in 2022.
Australian Associated Press
