Rafael Nadal's comeback came to a disappointing end as he was beaten 7-5 6-1 by Alex de Minaur at the Barcelona Open on Wednesday.
Nadal was playing his second match after picking up an injury in January but struggled to keep up with De Minaur, who is enjoying his best season on the ATP Tour yet after climbing into the top 10 on the rankings.
As for Nadal, he could next play at the Madrid Open at the end of next week - live on Sky Sports Tennis - in what could be his final season before retirement.
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Despite a huge roar from the home crowd as he came out onto court, Nadal was broken straight away by De Minaur in the first game. De Minaur also missed a chance to go a double break and 3-0 up against the 22-time Grand Slam champion.
Nadal punished him with a break of his own to make it 3-3 before the next four service games were shared. However, De Minaur continued to make good use of the drop shot and broke Nadal then held serve to win a 67-minute first set.
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Momentum was now firmly with De Minaur as the Australian missed a break point chance at the start of the third but broke Nadal in the third game to take a 2-1 lead.
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De Minaur broke for a second time which deflated the crowd again as Nadal lost out in one last effort to fight back. The 37-year-old dug deep but was broken again by De Minaur, who will face Daniel Altmaier or Arthur Fils in the third round.
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Britain's Cameron Norrie is still in the Barcelona Open and takes on home player Roberto Bautista Agut on Thursday, live on Sky Sports Tennis.
Draper fights back against Molleker in Munich
Britain's Jack Draper made an impressive comeback against Germany's Rudolf Molleker to book a spot in the quarter-finals of the Bavarian International in Munich.
Draper lost the opening set but came back from a rain delay renewed with energy and aggression as he won 4-6 6-1 6-1.
The 22-year-old, who is hoping to reach his first clay-court final at an ATP event, will face Taylor Fritz or Alejandro Moro Canas in the last eight on Friday, live on Sky Sports Tennis.
"He played an amazing level in the first set. The conditions were very rainy and slow, so it was tough to come out and play a certain way," said Draper.
"In the second and third, the sun came out and I started feeling better. better. I'm really proud of how I played.
"You've got to take whatever comes at you. It's a real challenge for both players and we both had to mentally stay good."
Wild card Molleker started the better player as he won the longer baseline rallies and capitalised on the only break point chances of the first set to go 3-2 up and went on to hold his serve.
Rain made the ball heavy and seemingly played into the German's hands in the set but play was stopped for 45 minutes ahead of the second set due to the wet weather.
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Immediately, Draper was visibly hitting the ball harder and broke to go 3-1 ahead after some brilliant play at the net and continued to be on the front foot as he won the remaining games in a quick 26-minute set.
A break at the start of the deciding set ensured Draper was now favourite and he carried the momentum for the remainder of the match by rattling off four games in a row to beat Molleker on his opponent's home turf.
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