Novak Djokovic suffered his earliest exit at the Italian open since 2013 when he was beaten by rising Danish star Holger rune in the quarter-finals.
The Serb top seed, who turns 36 next week, was beaten 6-2 4-6 6-2 by 20-year-old rune on the Rome clay.
Djokovic was bidding for his seventh title in the Italian capital as he prepares for the French open on 28 may.
Seventh seed rune will play Norwegian fourth seed Casper Ruud in the semi-final.
Djokovic’s preparations for the French open have been disrupted by injury, having missed the recent Madrid open with an elbow problem and returning to the court in Rome as he looked to build up form and fitness.
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The 22-time grand slam champion will have the opportunity at Roland Garros to move clear of Rafael Nadal in terms of the most men’s major titles of all time.
Following opening wins against Tomas martin Etcheverry, Grigor Dimitrov and British number one Cameron Norrie, Djokovic was going through the gears in Rome without yet finding his finest form.
There were signs of tension during a tetchy last-16 match against Norrie, before which Djokovic needed treatment for an injury that he was reluctant to discuss afterwards.
Djokovic, who will be replaced as world number one by Spain’s Carlos Alcaraz next week, also needed a medical timeout early in the second set against rune.
While that was perhaps a factor behind his flat performance, the main reason for the defeat was he could not cope with the problems posed by the Dane.