Britain’s Jack Draper let slip a third-set lead to fall just short of an upset against world number eight Andrey Rublev in the Madrid Open second round.
World number 121 Draper was 3-0 up in the third set but lost 2-6 6-4 7-5.
Draper, 20, has won four titles on the second-tier Challenger circuit this year – all on hard courts – and brought his momentum onto the clay at this prestigious Masters 1000 event.
But it was not quite enough against Rublev, who could face Dan Evans next.
Left-hander Draper had been impressive in his opening match against Italian world number 27 Lorenzo Sonego on Sunday and against the even higher ranked Rublev he stayed composed when he was taken to a third set.
He surged to a 3-0 lead in the decider but was pegged back as his first serve lacked consistency and Russian Rublev, playing under a neutral flag because of sanctions relating to Russia’s invasion of Ukraine, increased his level to win the contest after two hours and 19 minutes.
Last year Draper took a set off eventual champion Novak Djokovic at Wimbledon and also stunned Italian third seed Jannik Sinner at Queen’s and his two performances in Madrid are further evidence of a promising future.
Meanwhile, Serbia’s world number one Djokovic opened his campaign in the Spanish capital with a 6-3 6-2 win against Frenchman Gael Monfils.
Djokovic, 34, extended his 100% winning record over Monfils to 18 games – an ATP record for head-to-head dominance – and the victory also ensured he will remain at the top of the men’s rankings.
The 20-time Grand Slam champion is playing in only his fourth tournament of 2022 after not being allowed to compete at the Australian Open and events in the United States because he is unvaccinated against Covid-19.
“I’m still finding my form and my groove but I’m happy,” said Djokovic.
Later on Tuesday, Britain’s former world number one Andy Murray will take on Canadian 14th seed Denis Shapovalov in the second round.
And in the women’s event, British number one Emma Raducanu will chase a quarter-final spot when she faces Ukraine’s Anhelina Kalinina.