Three-time major champion Andy Murray from Great Britain won his 500th career hard-court match when he beat Canadian Denis Shapovalov 4-6, 7-6 (5), 6-3 in the first round of the Dubai Duty Free Tennis Championships on Monday.

Murray – who joined Roger Federer, Novak Djokovic, Andre Agassi and Rafael Nadal in the 500 club – said in a post-match interview that he “probably (doesn’t) have too long left but I’ll do the best that I can these last few months,” a possible hint that the 36-year-old is considering retirement.

No. 2 seed Andrey Rublev of Russia rallied past China’s Zhizhen Zhang 6-7 (4), 6-2, 6-4, while Polish third seed Hubert Hurkacz outlasted German Jan-Lennard Struff 7-6 (5), 6-7 (4), 7-6 (6). No. 7 seed Alexander Bublik also needed three sets to top Czech qualifier Tomas Machac 2-6, 6-3, 7-6 (5), and Dutchman Botic van de Zandschulp upset French sixth seed Adrian Mannarino 7-6 (3), 7-5.

American Sebastian Korda knocked off Russia’s Pavel Kotov 6-0, 6-2 in 54 minutes, and Tallon Griekspoor of the Netherlands led 7-5, 2-0 when Jordanian opponent Abdullah Shelbayh retired.

Abierto Mexicano Telcel Great Britain’s Jack Draper needed just 86 minutes to oust seventh-seeded Tommy Paul of the United States 6-0, 6-4 in the first round at Acapulco, Mexico.

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Draper never dropped his serve, shaking off three break points while converting four of his five break opportunities.

Third-seeded Alex De Minaur of Australia sailed into the second round with a 6-2, 6-1 blowout of Japan’s Taro Daniel.

The United States’ Ben Shelton rallied past Great Britain’s Daniel Evans 2-6, 7-5, 7-6 (5), and Serbia’s Miomir Kecmanovic came from behind to defeat Argentina’s Diego Schwartzman 4-6, 6-3, 6-1.

Austria’s Sebastian Ofner edged Mexico’s Ernesto Escobedo 6-7 (7), 6-4, 7-6 (4). In late matches, Japan’s Yoshihito Nishioka opposed Portugal’s Nuno Borges, fourth-seeded Taylor Fritz of the United States faced Italy’s Matteo Arnaldi, and Canada’s Felix Auger-Aliassime went up against Italy’s Flavio Cobolli.

Movistar Chile Open Sixth-seeded Facundo Diaz Acosta prevailed in an all-Argentine first round, rallying past Pedro Cachin 5-7, 6-3, 7-6 (2) on clay at Santiago, Chile.

In a match that lasted 3 hours, 8 minutes, Diaz Acosta won the last five points of the third-set tiebreaker.

Cachin had 18 break chances in the match but converted just three of them.

Another Argentine, Federico Coria, registered a 6-1, 7-6 (1) win over Slovakia’s Alex Molcan.

French qualifier Corentin Moutet upset seventh-seeded Roberto Carballes Baena 6-3, 7-5, 6-2, and Spain’s Pedro Martinez got past Italy’s Francesco Passaro 6-4, 6-1.