British number one Kyle Edmund saved seven match points before eventually losing to rising German star Alexander Zverev in the Italian Open last 16.
Edmund, who moved into the world’s top 20 this week, lost 7-5 7-6 (13-11) to the 21-year-old third seed.
World number six Juan Martin Del Potro has suffered an injury scare, retiring from his match with David Goffin.
World number two Rafael Nadal cruised past Canadian teenager Denis Shapovalov 6-4 6-1, while Marin Cilic also won.
The Croat fourth seed won 6-3 6-4 against France’s Benoit Paire and will play Spain’s Pablo Carreno Busta in the last eight.
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Edmund continues to push the big names
Edmund, 23, has claimed eye-catching scalps in 12-time Grand Slam champion Novak Djokovic and Bulgaria’s Grigor Dimitrov this year, helping the Yorkshireman rise into the top 20 for the first time in his career.
But he could not earn a notable victory against defending champion Zverev in Rome – despite pushing him hard throughout a gripping contest.
Edmund, now 19th in the world, became the first opponent to break Zverev in 65 service games to level at 5-5 in the first set, only to lose his own serve in the next game as Zverev went on to clinch the opener.
Zverev was searching for an 11th straight victory following back-to-back tournament wins in Munich and Madrid, finally sealing victory at the eighth attempt in a thrilling tie-break.
Zverev – who has won all three of his meetings with Edmund – will meet Goffin in the quarter-finals.
Injury concern for Del Potro
Belgium’s world number 10 Goffin was leading 6-2 4-5 when Del Potro, who had just missed a set point, retired with a groin injury.
Argentine Del Potro, 29, has been hampered by wrist problems in recent years.
But he has battled back to fitness and form over the past two years, winning his first ATP Masters title by beating Roger Federer at Indian Wells in March.
Shapovalov, considered one of the game’s rising stars, beat the 31-year-old Nadal in Montreal last year – but could not replicate the result on the Spaniard’s favoured clay surface.
Nadal will meet Italian home favourite Fabio Fognini, who beat Germany’s Peter Gojowczyk 6-4 6-4, in the last eight.
Serbia’s Novak Djokovic beat Spaniard Albert Ramos-Vinolas 6-1 7-5 to set up a quarter final against Japan’s Kei Nishikori who beat Germany’s Philipp Kohlschreiber 6-1 6-2.