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.”
Keys downs Gauff to reach Madrid Open quarter-finals
Madison Keys is through to the quarter-final of the Madrid Open for the first time in her career after rallying to a 7-6 (7-4), 4-6, 6-4 win over Coco Gauff on Monday.
The 29-year-old trailed 5-2 in the first set and 4-2 in the third set but rallied in both to come from behind to beat the number three seed.
Despite winning the second set, Gauff struggled to find her rhythm, suffering from 13 double faults, including two in the final game.
Keys will face former Madrid Open champion Ons Jabeur for a spot in the semi-final after the number eight seed overcame Jelena Ostapenko in straight sets.
Data debrief: Keys reaches new milestone
Having lost in the first round in seven of her nine previous trips to the Spanish capital, Keys has now bettered her previous best finish in Madrid - a third-round showing in 2016.
Keys hadn't won three matches in a row since reaching the US Open semifinals last year.
Keys downs Gauff to reach Madrid quarter-finals
Madison Keys is through to the quarter-final of the Madrid Open for the first time in her career after rallying to a 7-6 (7-4), 4-6, 6-4 win over Coco Gauff on Monday.
The 29-year-old trailed 5-2 in the first set and 4-2 in the third set but rallied in both to come from behind to beat the number three seed.
Despite winning the second set, Gauff struggled to find her rhythm, suffering from 13 double faults, including two in the final game.
Keys will face former Madrid Open champion Ons Jabeur for a spot in the semi-final after the number eight seed overcame Jelena Ostapenko in straight sets.
Data debrief: Keys reaches new milestone
Having lost in the first round in seven of her nine previous trips to the Spanish capital, Keys has now bettered her previous best finish in Madrid - a third-round showing in 2016.
Keys hadn't won three matches in a row since reaching the US Open semifinals last year.
Nadal goes the distance to reach Madrid Open last 16
Rafael Nadal battled to victory over three hours on the court against Pedro Cachin at the Madrid Open on Monday to seal a 6-1 6-7 (5-7) 6-3 win to reach the last 16.
The former world number one looked back to his best as he cruised through the opening set but was pushed hard in the second by Cachin.
Nadal came from behind to level at 5-5, but Cachin eventually sealed the set on his third set point.
The Spaniard then rallied in the third set, cutting down on his errors to regain control and advance to the fourth round at a tour-level event for the first time since 2022.
Nadal is one step away from booking his place in a 10th consecutive quarter-final in Madrid and will face Jiri Lehecka on Tuesday in the next round after the 30th seed overcame Brazilian qualifier Thiago Monteiro in two sets.
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