Novak Djokovic (7) vs. Learner Tien

A classic of the first-round genre — the elite veteran against an up-and-coming home hope — but amped up about as far as is possible. Tien, 19, has beaten four top-10 players this year with his parabolic serves and forehands and delicate mastery of ball control. Djokovic, 38, is all in on Grand Slams and loves drawing younger players, especially players like Tien, who thrive on craft and patterns, into a battle of soft skills that he is confident that he will win. The 24-time Grand Slam champion has not played since Wimbledon and will need to find his rhythm quickly against the American.

Jessica Pegula (4) vs. Mayar Sherif

Pegula came into last year’s U.S. Open with confidence after defending her Canadian Open title in Toronto and reaching the final of the Cincinnati Open. She was still searching for her first semifinal appearance at a major, having reached the quarterfinals six times.

She arrives at this year’s tournament as last year’s finalist, having crossed that Grand Slam bridge at her home major, but she also arrives with less confidence. Pegula has been in indifferent form for several events, and admitted in her pre-tournament news conference that she does not feel entirely confident in her game. Sherif is 2-7 against top-10 players in her career, but with Pegula defending so many ranking points in front of her home crowd, she will look to test her confidence.

Jessica Pegula comes into the last major of the year with points to defend from reaching the final. (Charly Triballeau / AFP via Getty Images)

Louis Armstrong

Start time: 11 a.m. ET, 9 a.m. PT
TV: ESPN, ESPN2, ESPN+, ABC

Emma Raducanu vs. Ena Shibahara (Q)

Raducanu’s 2021 title has not produced results in New York: She has not won a match at the U.S. Open since. But she comes into this event with a new coach in Francisco Roig, Rafael Nadal’s former lieutenant, on the back of one of her best runs of form since that famous run. Qualifier Shibahara, a doubles specialist who has made a push into singles, is unlikely to trouble her given that.

Emilio Nava (WC) vs. Taylor Fritz (4)

Two rock-solid talents at very different stages of their careers meet in an all-American clash. Nava is a wild card, but he won the USTA Challenge, which rewards recent hard-court performance, to get it. Fritz is last year’s beaten finalist and the top name on a long list looking to end a Grand Slam drought for the U.S. on the men’s side. Fritz is likely to have too much firepower on serve and too much solidity on return, but Nava is going to be challenging top players in the early stages of majors for some time.

Destanee Aiava (Q) vs. Jasmine Paolini (7)

Paolini, beaten by Świątek in the Cincinnati Open final, has backed up last year’s two major finals with a presence in the later rounds of some WTA 1000 events — but not with strong performances in the majors themselves. She starts her campaign against Australia’s Aiava, who edged out the rising German talent Ella Seidel to get through qualifying.

Daniil Medvedev (13) vs. Benjamin Bonzi

Medvedev is in a bad spot. The archetypal big-serving counterpuncher, who made Djokovic and Rafael Nadal evolve their baseline games when he came onto the scene, has lost some zip on his serve and some punch in his counterpunch. Bonzi beat him at Wimbledon, and Medvedev is firmly on upset watch here, to the point that whether or not it would be an upset is in question.

Taylor Fritz is on a mission to win a first Grand Slam title at his home major. (Kirsty Wrigglesworth / Associated Press)

Grandstand

Start time: 11 a.m. ET, 9 a.m. PT
TV: ESPN, ESPN2, ESPN+, ABC

Jakub Menšík (16) vs. Nicolás Jarry

A tough assignment for Menšík, the prodigiously talented teenager who has some early-career baggage at majors which mostly consists of close defeats in matches he might have put away. Expect a lot of serve and first shot in this one, as Jarry can go toe-to-toe with the Czech, and both players can struggle on rally tolerance. If Menšík loses focus, the Chilean will be ready to take advantage.

Alexandra Eala vs. Clara Tauson (14)

Eala’s first year on the tour has made her a star for the Philippines, and she’s upset some top players. Tauson, a formidable ballstriker but not always comfortable when maneuvered left and right, may find the lefty’s craft and use of angles tricky.

Emma Navarro (10) vs. Wang Yafan

If Pegula is in a tricky moment, Navarro is in a very difficult one. Ever since a thrashing at the hands of Jéssica Bouzas Maneiro at the French Open in which she lost the first set 6-0, the American — usually the epitome of confident, aggressive consistency — has been searching for form. She ought to get a win in her opener here, but she defends semifinal points and is still figuring out how to live with a much smaller number next to her name than there was 12 months ago.

Brandon Nakashima (30) vs. Jesper de Jong (Q)

Nakashima is one of the most consistent players among the American men: a hugely underrated spot serve with impeccable match toughness. De Jong, a trickster with winners to burn and an eye for flair, will look to disrupt Nakashima’s rhythm and try to unglue him from the baseline; Nakashima will do his best to put the Dutchman to sleep with a tennis metronome.

Around the grounds

Start time: 11 a.m. ET, 9 a.m. PT
TV: ESPN, ESPN2, ESPN+, ABC

Rebecca Marino (Q) vs. Leylah Fernandez (31)

Second on Stadium 17: An all-Canadian clash and a test for Fernandez’s recent hard-court form which saw her win the WTA 500 title at the Citi Open in Washington, D.C.

Stefan Dostanic (WC) vs. Eliot Spizzirri (WC)

Second on Court 11: An all-American wild card clash. Spizzirri beat rising phenom João Fonseca in qualifying last year, while Dostanic won the college tennis wild card playoff to make his first main draw in New York. Big for both of them.

Janice Tjen (Q) vs. Veronika Kudermetova (24)

First on Court 13: Victoria Mboko and Loïs Boisson’s Canadian and French Open runs looked like Cinderella stories, but they were built on relentless winning in the tennis minor leagues. The next player from that never-lose school is Tjen, an Indonesian who plays college tennis at Pepperdine. Upset alert is on.

Tell us the matches you are looking out for in the comments.

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(Top photo of Emma Raducanu: Getty Images)