Novak Djokovic returned to action at the Monte-Carlo Masters with a comfortable victory but Jack Draper was narrowly beaten while Carlos Alcaraz pulled out through injury.
The Spaniard, recently overtaken as world number two by Jannik Sinner, had been due to face Felix Auger-Aliassime in the second round after receiving a first-round bye but is struggling with a forearm problem.
Alcaraz wrote on social media: “I have been working in Monte Carlo and trying to recover until the last minute from an injured pronator teres in my right arm, but it was not possible and I cannot play! I was really looking forward to playing… See you next year!”
The 20-year-old won his first title since last summer’s Wimbledon in Indian Wells last month but was then beaten by Grigor Dimitrov in the quarter-finals of the Miami Open.
It is an important part of the season for Alcaraz, who is due to defend his titles in Barcelona and Madrid over the next month. He has been replaced in the draw by Italy’s Lorenzo Sonego.
Djokovic played his first match since Indian Wells after choosing to skip Miami and then parting ways with long-time coach Goran Ivanisevic.
With former Serbian doubles specialist Nenad Zimonjic guiding him from the stands, Djokovic, now the oldest men’s singles number one in history, eased to a 6-1 6-2 victory over Russia’s Roman Safiullin.
The 36-year-old said on Sky Sports: “I’m very pleased. Even the games that I lost, I had break points in those games. Really good first match at the start of the clay season. I hope to maintain this rhythm.”
Draper took on 10th seed Hubert Hurkacz and for the second year in a row lost a very tight contest.
The British number two forced a deciding set and then broke Hurkacz, champion on clay in Estoril last week, when he served for the match at 5-4 but the Pole played a brilliant tie-break to win 6-4 3-6 7-6 (2).
Draper’s exit ends British interest in singles, with Cameron Norrie and Dan Evans also losing in the first round.
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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