Rafael Nadal’s latest comeback bid came to an end as he was well beaten 7-5 6-1 by fourth seed Alex de Minaur at the Barcelona Open.
The 37-year-old was playing just his second tournament in 15 months after suffering another hip problem at his comeback event in Brisbane in January.
And having intimated that this will be his final year before retirement, Nadal’s defeat was likely to mark his final appearance at a tournament he has won 12 times.
Having overcome Italian Flavio Cobolli in the opening round, Nadal faced a much sterner test against the in-form De Minaur and was sent scampering around the court in a tight opening set which was edged by the Australian.
De Minaur went on to step up a gear, securing a double break over the Spaniard and racing over the line behind a strong service game on which he did not drop a single point in the second set.
Jack Draper made the most of a rain delay to defeat wild card Rudolf Molleker and reach the quarter-finals of the BMW Open in Munich.
German Molleker, ranked 179th, had been the better player in the first set but a brief stoppage ahead of the second set changed the momentum of the contest.
Draper began to assert his powerful game after the resumption and lost only two more games, pulling away to claim a 4-6 6-1 6-1 victory.
In the last eight the British number two, who is ranked 46th, will take on either third seed Taylor Fritz or Spanish qualifier Alejandro Moro Canas.
Speaking in an on-court interview, Draper said: “I think Rudy played an amazing level in the first set. The conditions were very rainy and very slow. In the second and third, the sun comes out and I start feeling better. I’m really proud of the way I played.”
Nadal slumps out of Madrid Open as farewell appearance comes to a halt
Jiri Lehecka claimed a memorable win over one of tennis' greats as he downed Rafael Nadal at the Madrid Open.
Nadal's farewell appearance at the tournament he has won five times came to an end with a 7-5 6-4 defeat on Tuesday.
The 22-time grand slam champion had been hoping to tee up a quarter-final against Daniil Medvedev.
Ultimately, though, world number 31 Lehecka was the man who progressed.
Lehecka ruined the hopes of the Nadal fans packed into the stands in the Spanish capital, and took control when he reeled off 10 straight points to take the opening set.
Nadal won the Madrid Open in 2008, 2010, 2013, 2014 and 2017, and said farewell to the crowd in an on-court interview following his defeat.
Data Debrief: Nadal falls short of milestone
Nadal had been hoping to win his 60th match at the Madrid Open, while he would have reached his 100th ATP Masters 1000 quarter-final had he won. This was his first defeat to a player ranked lower than 20th in the world since he went down to Pablo Cuevas in 2016.
Lehecka, meanwhile, will make his second appearance in the last eight of a Masters 1000 event.
Auger-Aliassime gets the better of Ruud as Medvedev hits Masters 1000 milestone
Casper Ruud's hopes of building on his victory at the Barcelona Open were ended as he lost to Felix Auger-Aliassime at the Madrid Open.
Auger-Aliassime will now face top seed Jannik Sinner in the quarter-finals, after claiming a 6-4 7-5 victory over the fifth seed Ruud on Tuesday.
Ruud, runner-up at last year's French Open and a force to be reckoned with on clay, won in Barcelona earlier in April, but came unstuck against the Canadian.
It was not the only shock exit, as Alexander Zverev, the world number five, succumbed in straight sets to Francisco Cerundolo.
Earlier, Daniil Medvedev claimed his place in the quarters, in which he could face Rafael Nadal, by beating Alexander Bublik 7-6 (7-3) 6-4.
Data Debrief: Medvedev's milestone
Five of the six quarter-finals Medvedev has reached on clay have come at either ATP Masters 1000 or grand slam level.
He has now reached at least the quarter-final stage at all nine Masters events, too.
Alcaraz matches Nadal record as reigning champion scrapes into Madrid Open quarters
Jan-Lennard Struff made life difficult for Carlos Alcaraz, but the reigning Madrid Champion eventually made it through.
Alcaraz had won both of his opening games with the minimum of fuss, but he needed three sets to get beyond Struff, who won a second-set tie-break.
However, Alcaraz eventually prevailed in the decider, clinching a 6-3 6-7 (5-7) 7-6 (7-4) victory.
Alcaraz, who is in the hunt for a third straight title in Madrid, will now face seventh-seed Andrey Rublev for a place in the last four.
Data Debrief: Prodigal son matches the master
There have been plenty of comparisons between Alcaraz and his fellow Spaniard Rafael Nadal.
And with his win on Tuesday, Alcaraz matched Nadal's record for the longest winning run at the Madrid Open, at 14 matches, since the tournament began in 2002.
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