Serena Williams Will Play Danka Kovinic at U.S. Open on Monday

Unseeded and ranked No. 608, the great Serena Williams could have been drawn to face all manner of opposition in the opening round of her farewell U.S. Open.

She could have played any of the 32 seeds, including the No. 1 seed, Iga Swiatek, or the No. 7 seed and her longtime rival, Simona Halep, now working with Williams’s former coach Patrick Mouratoglou.

Williams could have had a U.S. Open rematch with Naomi Osaka or Bianca Andreescu, both of whom have beaten her in recent U.S. Open finals. She could have matched up, for the first and final time, with Coco Gauff, an 18-year-old American star who chose tennis in part because Williams was such an inspiring and dominant champion.

Or, most poignantly, Serena could have faced the deeply symbolic and forever-conflicted prospect of playing her big sister Venus Williams one last time in the tournament in which both came of age — to put their enduring excellence in perspective — in a different century.

But tennis draws are roulette wheels, and Thursday’s game of chance in New York delivered Danka Kovinic, a first-round opponent lacking resonance and the intimidation factor but hardly lacking the ability to snuff out Serena Williams’s last chance at a last hurrah.

Kovinic, an unseeded 27-year-old Montenegrin who trains in the Serbian capital, Belgrade, is ranked just 80th in the world and has lost her last five singles matches on tour. But Williams, who turns 41 on Sept. 26, is ranked far below Kovinic at this late stage of her career and has only a 1-3 record in singles since returning to the tour in June.

She was soundly beaten, 6-4, 6-0, by Emma Raducanu, last year’s surprise U.S. Open champion, in the opening round of the Western and Southern Open last week, with Williams wearing tape to protect her left knee and looking late to the ball and increasingly glum.

In light of her recent form, advanced tennis age and lack of matches this season, a deep run at her final U.S. Open would be one of Williams’s most remarkable achievements.

But first she must find the means to defeat Kovinic. They have never played in singles on tour, but Kovinic has the weapons, including a powerful serve, to trouble Williams in a match that also will be, given the circumstances, an event. It will be played on Monday in Arthur Ashe Stadium, surely at night under the prime-time lights.

The occasion could certainly get to Kovinic, much more accustomed to outside courts. But she has handled the big stage well before: upsetting Raducanu in the second round of this year’s Australian Open in Margaret Court Arena. The occasion and scenario could also get to Williams, a champion who runs on emotion and has made it clear she is no fan of goodbyes.

But there is a huge gap in achievement here: Williams is clearly the greatest women’s player of this era with 23 Grand Slam singles titles and long runs at No. 1. Kovinic has yet to win a tour singles title.

If Williams, a six-time U.S. Open singles champion, were to prevail, she is likely to face the No. 2 seed, Anett Kontaveit, in the second round. Though that sounds like a nasty draw, Kontaveit built her lofty ranking on the strength of increasingly distant success and has struggled since March, in part because of the aftereffects of contracting Covid-19.

She is arguably the most vulnerable of the top eight seeds, which means that Williams, if she can pull her big game together and keep her aches and pains to a minimum, has actually landed in a decent place in her last U.S. Open.

It is harder to say that about Venus Williams, 42, in what could also be her final U.S. Open. She has not won a singles match on tour in over a year and will be the underdog in her first-round match against Alison Van Uytvanck, a Belgian ranked No. 42. If she gets past that, Venus would most likely face Elena Rybakina, the reigning Wimbledon champion, whose big serve, lean build, easy power and athleticism bear a certain resemblance to Venus.

What seems clear is that Venus and Serena, who are in different halves of the draw, will not play each other again, at least not on tour, after facing off 31 times in singles over more than 20 years. (Serena leads, 19-12.)

Swiatek, who won the French Open in June, has lost in the quarterfinals or earlier in her last four tournaments but showed excellent form on American hardcourts earlier this season, winning the BNP Paribas Open in Indian Wells, Calif., and the Miami Open en route to a 37-match winning streak in singles. Her first-round opponent at the U.S. Open will be Jasmine Paolini, an unseeded Italian ranked 57th.

Raducanu, who has yet to reach another tournament final since her shock triumph in New York last September, has shown flashes of better form recently, with back-to-back routs of Serena Williams and Victoria Azarenka last week. But she has a daunting first-round matchup in New York in the French veteran Alizé Cornet, an Australian Open quarterfinalist this season and one of the best defenders and competitors on tour. Cornet also upset Swiatek in the third round of Wimbledon this year.

But the best matchup of the opening round in the women’s tournament could be Osaka versus Danielle Collins.

Osaka, a former No. 1 and two-time U.S. Open singles champ, is unseeded this year but still dangerous on hardcourts as she showed by reaching the Miami Open final earlier this season. Collins, a fiery American seeded 19th, reached the Australian Open singles final in January, losing to Ashleigh Barty, the now-retired Australian star.

Unless Swiatek can recover her early-season form, it looks like a wide-open women’s tournament, and the men’s event also could be full of surprises in the absence of Novak Djokovic, the former No. 1 and reigning Wimbledon champion, who withdrew from the U.S. Open on Thursday shortly before the draw because he continues to be barred from entering the United States as he is not vaccinated for Covid.

Whatever one’s view of Djokovic’s stance, he has stuck to his principles at considerable cost to himself and his sport, which has often been deprived of one of its biggest stars.

Djokovic has refused to be vaccinated though nearly all of tennis’s top 200 players and all of Djokovic’s significant rivals have done so. The choice has caused him to miss four Masters 1000 events this year and two Grand Slam tournaments (the Australian Open and the U.S. Open) at a moment when he and Rafael Nadal are locked in a duel for the men’s record for major singles titles.

Though Djokovic did win Wimbledon this year, he received no ranking boost for it because the men’s and women’s tours stripped Wimbledon of ranking points because the tournament had barred Russian and Belarusian players in response to Russia’s invasion of Ukraine.

To sum up, it has been a tennis season that beggars belief, full of abrupt twists and turns. Though the Russians and Belarusians will be in New York, Djokovic will not and must now wait and lobby to be allowed to play next year’s Australian Open, which would require the new Australian government to lift his three-year ban on applying for a visa, a ban that resulted from his deportation in January.

In Djokovic’s absence in New York, Nadal, who has 22 Grand Slam singles titles to Djokovic’s 21, has a clearer pathway to padding his slim lead. He has a seemingly smooth early-round draw, facing Rinky Hijikata, an inexperienced wild-card entry from Australia, in his opening match.

But Nadal has played (and lost) just one match since withdrawing from Wimbledon in July because of an abdominal injury. Daniil Medvedev of Russia, who is the No. 1 men’s seed and defending champion after defeating Djokovic in last year’s final, has hardly been an irresistible force this season, even on his preferred hardcourts.

There is elbow room, perhaps plenty of elbow room, for others to muscle their way into the title picture: men such as Carlos Alcaraz, Stefanos Tsitsipas, Taylor Fritz, Jannik Sinner, Nick Kyrgios or the surprise Cincinnati champion, Borna Coric. (This is not an exhaustive list.)

But that is a matter for the second week of this intriguing U.S. Open. For now, all eyes are on Serena.