Milos Raonic extended his unbeaten ATP Head2Head record against Denis Istomin on Tuesday, defeating the 33-year-old 6-2, 6-2 at the Delray Beach Open by VITACOST.com.

The second seed dropped just one point behind his first serve (21/22) and broke serve on four occasions to advance in 65 minutes. Australian Open quarter-finalist Raonic has won each of his five encounters against Istomin in straight sets.

With his fifth win of the 2020 ATP Tour season, Raonic improves to 6-1 at this event. In 2017, the Canadian beat Kyle Edmund and Juan Martin del Potro in back-to-back matches to advance to the championship match on his tournament debut.

Raonic will face Cedrik-Marcel Stebe in the second round. Stebe saved five of six break points to defeat lucky loser Bernard Tomic 6-2, 3-6, 6-2 in one hour and 39 minutes.

Cameron Norrie withstood 13 aces to beat third seed Taylor Fritz 6-4, 6-7(4), 6-4. The British qualifier, making his second appearance at the ATP 250 event, will meet American wildcard Brandon Nakashima for a quarter-final spot. Nakashima claimed his maiden ATP Tour victory on Monday, beating recent Pune champion Jiri Vesely 7-6(4), 6-1.

Auckland champion Ugo Humbert also advanced to the second round, rallying from a set down to beat lucky loser Stefan Kozlov 6-7(5), 6-3, 6-1. Humbert served 12 aces and converted seven of 11 break points throughout the two-hour, 26-minute encounter.

Petros Tsitsipas/Stefanos Tsitsipas were mere points from a stunning first-round upset on Tuesday against reigning Roland Garros champions Kevin Krawietz/Andreas Mies, but the top seeds regrouped for a 6-4, 6-7(5), 10-6 win at the Open 13 Provence in Marseille.

Krawietz/Mies snapped a four-match losing streak by advancing in one hour and 29 minutes. They’ll turn their attention to a quarter-final battle with Benoit Paire/David Vega Hernandez, who beat Alexander Bublk/Alexei Popyrin 4-6, 6-2, 10-5.

Frederik Nielsen/Tim Puetz scored the upset of the day by taking out third seeds Jamie Murray/Neal Skupski 3-6, 6-3, 10-8. Next up for them are Rohan Bopanna/Denis Shapovalov, who rallied to overcome Simone Bolelli/Jannik Sinner 6-7(6), 6-3, 10-6. Jonathan Erlich/Andrei Vasilevski rounded out play in Marseille by taking out Cheng-Peng Hsieh/Denys Molchanov 7-6(3), 6-3.

At the Delray Beach Open by VITACOST.com, Nicholas Monroe/Jackson Withrow eased past Adrian Mannarino/Mackenzie McDonald 7-6(3), 6-3. Awaiting them in the quarter-finals are fourth seeds Luke Bambridge/Ben McLachlan, who advanced via walkover against John Millman/Matt Reid.

Second seeds Lukasz Kubot/Marcelo Melo headline doubles action at the Rio Open presented by Claro as they take on Pablo Cuevas/Fernando Verdasco.

Jannik Sinner made a winning start to his debut Open 13 Provence campaign on Tuesday, beating Norbert Gombos 6-4, 7-6(5) in Marseille.

The reigning Next Gen ATP Finals champion, who trailed the second-set tie-break 1/4, saved all six break points he faced throughout the two-hour, three-minute encounter. Sinner is competing at a career-high No. 68 in the FedEx ATP Rankings this week. At last week’s ABN AMRO World Tennis Tournament in Rotterdam, the Italian recorded his maiden Top 10 victory against David Goffin to reach his first ATP 500 quarter-final.

That is RIDICULOUS @janniksin ?

Just how have you done that?!

?: @TennisTV | @Open13 pic.twitter.com/gpNkQmvd0d

— ATP Tour (@atptour) February 18, 2020

Sinner will face top seed Daniil Medvedev in the second round. Medvedev is making his second appearance in the main draw this year. The World No. 5 advanced to the quarter-finals on his tournament debut in 2017.

In the first match on Court Central, Hubert Hurkacz needed just 64 minutes to move past French wild card Antoine Hoang 6-4, 6-1. The eighth seed dropped just two points behind his first serve (22/24) to book a second-round clash against Vasek Pospisil. The Montpellier runner-up saved five of six break points to beat Emil Ruusuvuori of Finland 7-6(6), 6-3.

Carlos Alcaraz cites Rafael Nadal as his tennis idol and his heavy topspin groundstrokes could be viewed as a tribute. But the 16-year-old Spaniard sees his game more closely resembling another ATP Tour legend.

”I like to play very aggressively, with a lot of winners. My style is more or less like Roger Federer’s, aggressively coming to the net and playing a lot of drop shots,” Alcaraz said.

Alcaraz has already accomplished something that Federer could not: winning his ATP Tour debut. The 16-year-old defeated Albert Ramos-Vinolas on Monday at the Rio Open presented by Claro, outlasting the veteran Spaniard in a third-set tie-break that finished at 3:00am after three hours and 36 minutes.

He made fans sit up and take notice with his outstanding play, pushing Ramos-Vinolas around the baseline for much of their clash. Alcaraz tirelessly chased down balls in the early morning hours and held his nerve to close out the biggest moment of his fledgling career.

The 16-year-old has largely eschewed junior tournaments for pro events and has already made noise on the ATP Challenger Tour. Last year, the then-15-year-old defeated reigning Next Gen ATP Finals champion Jannik Sinner at a Challenger in Alicante, becoming the first player born in the year 2003 to win a match at that level. The following week in Murcia, he became just the fifth player aged 15-and-under in the past 20 years to defeat a Top 200 player.

Alcaraz’s talent was quickly noticed by former World No. 1 Juan Carlos Ferrero, who now coaches the young Spaniard. Ferrero is confident that his pupil could soon find himself in the mix as a contender for the biggest titles on the ATP Tour.

“He’s only 16 and he’s just starting to travel the world. He has the level, the speed, he’s getting better physically every day, so I think he can be one of the best,” Ferrero said. “I don’t know how high, but I think he can be up there in two or three years. I have a lot of experience with what he is going to deal with, [so] I’m giving him the best advice that I can.”

Alcaraz has been soaking in the week in Rio, making the most of his training sessions with top players and viewing his match with Ramos-Vinolas as an invaluable learning experience. The modest teenager is content to listen for now, preferring to let his racquet do the talking when he steps on court.

”When I spend time with tennis greats like Rafa or Ferrero or any other player, I don’t say anything. I listen to everything they say because it is very valuable to me,” Alcaraz said. “In each tournament I go to, I try to do my best. If that happens, then I will gradually go up.”

Orlando Luz/Rafael Matos kicked off doubles action at the Rio Open presented by Claro with a huge upset on Monday night, delighting the home crowd with a 6-1, 4-6, 10-8 victory over top seeds Juan Sebastian Cabal/Robert Farah.

Neither Luz or Matos had won a tour-level match before, but they held their nerves and took the last three points of the Match Tie-break to prevail in one hour and 28 minutes. Luz/Matos have won two doubles titles together on the ATP Challenger Tour.

At the Open 13 Provence in Marseille, second seeds Wesley Koolhof/Nikola Mektic saved a match point to defeat Tomislav Brkic/Marin Cilic 7-5, 1-6, 12-10. Koolhof/Mektic fought back from 9/10 in the Match Tie-break before converting their third match point to reach the quarter-finals.

The Delray Beach Open by VITACOST.com saw Nikola Cacic/Hugo Nys score a 6-4, 2-6, 10-4 first-round upset against Santiago Gonzalez/Ken Skupski. Cacic/Nys raced through the Match Tie-break to advance in one hour and 30 minutes.

Third-seeded Chilean Cristian Garin was pushed to the brink on Monday at the Rio Open presented by Claro, but converted his eighth match point to outlast Slovakian Andrej Martin in a wild 4-6, 7-5, 7-6(5) first-round battle.

Garin fought back from 2-4 in the final set, but let slip four match points with Martin serving at 5-6. The Chilean built a 6/2 lead in the tie-break and made good on his last chance to prevail after three hours and 10 minutes.

He is now on a five-match winning streak after taking the title two weeks ago in Cordoba (d. Schwartzman). Next up for Garin is Argentine Federico Delbonis, who scored a convincing 6-2, 6-4 win over Spaniard Roberto Carballes Baena.

Pablo Andujar scored the upset of the day by defeating ninth seed Fernando Verdasco 6-3, 6-3 in an all-Spanish battle. Andujar broke Verdasco five times en route to tying their ATP Head2Head series at 3-3.

Awaiting him in the second round is another Spaniard in qualifier Pedro Martinez, who rallied to defeat Bolivian Hugo Dellien 3-6, 6-2, 7-5. The 22-year-old is still flawless (4-0) in first-round matches this season.