First round singles action continues on Monday in New York.

In a truly baffling decision, soon-to-be-retired Stan Wawrinka was not initially rewarded a wild card into this event. But after a withdrawal this past week, the 2016 champion was finally invited to the end-of-summer party. And at the second Major in a row, he draws Matteo Berrettini in the first round, in what could be Wawrinka’s last match at a Grand Slam tournament.

Monday also provides several other appetizing first round contests, such as two-time Major runner-up Stefanos Tsitsipas taking on recent Cincinnati champ Arthur Fils. Plus, top names like Aryna Sabalenka, Iga Swiatek, and Naomi Osaka make their 2016 US Open debuts. And defending champion Carlos Alcaraz makes his long-awaited return from injury, in his first match since April.

Here’s a rundown of the most notable matches on Day 2 (in chronological order, all times local):

Stefanos Tsitsipas vs. Arthur Fils (10) – 11:00am on Louis Armstrong Stadium

Amazingly, despite earning only one match win at a Major this season, Fils sits at No.5 in the year-to-date rankings. He has won 31 matches outside of the Majors during 2026, and just a week ago collected the biggest title of his career in Cincinnati. The 22-year-old Frenchman is a perfect 5-0 against Tsitsipas, who is now ranked outside the top 50, and owns a losing record at this event.

Aryna Sabalenka (1) vs. Camila Osorio – 11:30am on Arthur Ashe Stadium

Sabalenka is 40-8 on the year, but has struggled since suffering a big upset in the Roland Garros quarterfinals at the hands of Diana Shnaider, despite being up a set and two breaks. Aryna is the two-time defending champion, and is 2-0 against Osorio, a 24-year-old Columbian who is on a four-match losing streak in New York.

Ashlyn Krueger vs. Amanda Anisimova (10) – Second on Louis Armstrong Stadium

Anisimova is the player who Sabalenka defeated to win this title a year ago, but the two-time Major finalist has gone just 20-11 in a 2026 season that was interrupted by a wrist injury. She’s 1-0 against Krueger, a fellow American who advanced to the round of 16 earlier this summer at Wimbledon.

Roman Safiullin vs. Carlos Alcaraz (2) – Second on Arthur Ashe Stadium

Alcaraz has not played a match since suffering a wrist injury this past April in Barcelona. But he’s claimed three of the last four Majors he’s attended, and will be eager to add to his Major title in the absence of his main rival, Jannik Sinner. Alcaraz has split two prior encounters with Safiullin, with the 29-year-old taking their only hard court meeting, three years ago at the Paris Indoors.

Matteo Berrettini vs. Stan Wawrinka (WC) – Third on Grandstand

At The Championships, Berrettini defeated Wawrinka in a four-setter that lasted well over four hours, with each set decided by a tiebreak. Neither player arrives at this rematch in great form: Matteo is just 18-15 on the year, while Stan is 9-18 on the year at al levels. This match could very well be the end of Wawrinka’s stellar Major career, which saw him prevail in all three Major finals he appeared in, defeating the World No.1 in all three of those finals.

Katie Volynets vs. Linda Noskova (6) – Third on Court 11

In another baffling decision by the tournament, Noskova has been placed on an outer court, just weeks after becoming a Major champion at Wimbledon. She’s a modest 3-4 lifetime at the US Open, though I’m curious to see if Noskova can build upon the momentum she brings in from the last Major. Volynets is a 24-year-old American who just this past week won a lower-level title in Philadelphia.

Ben Shelton (8) vs. Tallon Griekspoor – Not Before 7:00pm on Arthur Ashe Stadium

Given the injuries of Sinner and Alcaraz, this is a huge opportunity for Shelton to win his first Major title. He’s a two-time semifinalist at hard court Majors, and earlier this month the 23-year-old successfully defended his Masters 1000 title in Canada. Griekspoor also enjoyed a good tournament in Canada, where he upset top-seeded Alexander Zverev. However, the 30-year-old Dutch has lost in the first round of the last five Majors.

Iga Swiatek (8) vs. Xiyu Wang – Not Before 7:00pm on Louis Armstrong Stadium

Swiatek was the WTA champion this month in Canada, and followed that up with a semifinal run in Cincy. The 2022 champion is 2-0 against Xiyu, with a pair of straight-set victories on clay over the 25-year-old from China.

Naomi Osaka (13) vs. Anastasia Zakharova – Last on Arthur Ashe Stadium

A year ago at this event, Osaka achieved her first Major semifinal since 2021. She’s logged some nice results this summer, as Naomi finally gained some traction on grass, and was a quarterfinalist in both Washington and Toronto. Zakharova is a 24-year-old who, as per Tennis Abstract, is 0-7 lifetime against top 20 players.

Monday’s full Order of Play is here.