While Wimbledon is known to have had some of the best finals in men’s tennis history, the U.S. Open has had a few memorable conclusions of its own. From a McEnroe vs Borg rematch to Roger Federer making history, see which memorable matches crack this Betway Insider top 10 list of the all-time greatest men’s singles finals.

When is the U.S. Open Men’s Final?

The 2023 U.S. Open tennis tournament’s men’s singles final is scheduled for Sunday, Sept .10.

What time is the U.S. Open Men’s Final?

The 2023 U.S. Open men’s singles final will take place at 4 p.m. on Sept. 10.

U.S. Open Men’s Finals History

In the inaugural U.S. Open men’s final, played in 1881, American Richard Sears captured the first of his seven U.S. Open championships, which ties him for the all-time men’s singles record. The most recent final, in 2022, was won by Spaniard Carlos Alcaraz over Norwegian Casper Ruud.

Arthur Ashe won the first U.S. Open title of the Open Era in 1968. Click here for the full list of winners of the U.S. Open men’s singles championship.

Who has won the most U.S. Open Men’s titles?

If you include all the years when only amateurs were eligible for the tournament, then Bill Tilden, William Larned, and Richard Sears share the record for the most U.S. Open men’s singles titles with seven apiece.

Looking only at tennis’ Open Era (post-1968), when professionals were included, Roger Federer, Pete Sampras, and Jimmy Connors are tied for the record with five championships apiece.

Ranking the Top 10 Greatest U.S. Open Men’s Finals of all time

  1. No. 2 Daniil Medvedev defeats No. 1 Novak Djokovic in 2021

Match Result: 6-4, 6-4, 6-4

After a nightmare 2020, Novak Djokovic was on top of the world in 2021. He had won the first three legs of the 2021 Grand Slam and was looking to become the first man since 1969 to complete the full four in the same calendar year.

At the U.S. Open, however, Djokovic ran into No. 2 Daniil Medvedev, who is notoriously far more prolific on hard courts than on any other surface. He was so dominant in the 2021 final that Djokovic didn’t even take a set off him.

"It's the first time I'm so nervous saying my speech…sorry for you fans and Novak because we all know what he was going for today,” Medvedev said after winning.

  1. No. 5 Arthur Ashe defeats No. 8 Tom Okker in 1968

Match Result: 14-12, 5-7, 6-3, 3-6, 6-3

The 1968 U.S. Open men’s final was the first of the Open Era, but there were still some amateurs competing in the competition. One of those amateurs was American Arthur Ashe, a lieutenant in the U.S. Army at the time.

Ashe beat fellow American amateur Clark Graebner in the semifinals to set up a matchup with eighth-seeded Tom Okker in the final. In an era with no tiebreaks, the first set went an astonishing 26 games. This was indicative of the extremely close match -- which Ashe would ultimately win in five sets. With the victory, Ashe became the first African American to win a major men’s tennis championship.

  1. No. 2 Andre Agassi defeats No. 7 Todd Martin in 1999

Match Result: 6-4, 6-7 (7-5), 6-7 (7-2), 6-3, 6-2

Pete Sampras and Patrick Rafter both missed the 1999 U.S. Open, making the tournament Andre Agassi’s to lose. He faced fellow countryman Todd Martin, the world’s No. 7-ranked player, in the final.

Agassi lost two tiebreakers and found himself down two sets to one. He was struggling with Martin’s serve, which recorded 23 aces. A late break in the fourth set evened the score, and Agassi coasted from there to his second U.S. Open title.

“'I'll tell you what, how can you ask for anything more than two Americans in the final of the U.S. Open playing a great five-set match? Win or lose, this is the greatest time of my life. I'll never forget New York right here,” Agassi said after the match.

  1. No. 3 Pancho Gonzalez defeats No. 1 Ted Schroeder in 1949

Match Result: 16-18, 2-6, 6-1, 6-2, 6-4

In an era before tiebreaks, Pancho Gonzalez lost perhaps the most heartbreaking first set in U.S. Open history. He then dropped the second one to fall behind 2-0 in the match.

Gonzalez would win as many points over the next three sets as opponent Ted Schroeder won in the first, and that would be enough to make him the first man to come back from a two-set deficit in a U.S. Open final. A full 71 years would go by before Dominic Thiem repeated the feat in 2020.

  1. No. 2 Rafael Nadal defeats No. 5 Daniil Medvedev in 2019

Match Result: 7-5, 6-3, 5-7, 4-6, 6-4

Rafael Nadal’s usual rivals were gone before the 2019 U.S. Open final arrived. Novak Djokovic had retired in the fourth round, and Roger Federer lost in the quarterfinals of what would end up being his last U.S. Open. With those two big names out of the picture, Nadal drew hard-court master Daniil Medvedev in the final. Medvedev was looking for his first Grand Slam title.

Despite romping through the first two sets, Nadal struggled in the next two, and the match went the distance. It didn’t matter, because the 33-year-old Spaniard had just enough left in him to send his Russian opponent packing.

  1. No. 2 Dominic Thiem defeats No. 5 Alexander Zverev in 2020

Match Result: 2-6, 4-6, 6-4, 6-3, 7-6 (8-6)

Dominic Thiem and Alexander Zverev are not only rivals but also good friends. It was only fitting that they should meet in the final of the 2020 U.S. Open, which was overshadowed by the ongoing COVID-19 pandemic. There were no fans in the stands to watch the match live, but despite the atmosphere, this was a final that featured three remarkable firsts.

  1. Dominic Thiem became the first man in the Open Era to rally from a two-set deficit and win the final.
  2. The fifth set in a men’s U.S. Open championship match was decided by a tiebreak for the first time.
  3. Thiem became the first Austrian man to win the U.S. Open.

A remarkable fifth set saw both men fight off championship points.

“I wish we could have two winners today,” said Thiem.

  1. No. 6 Juan Martin del Potro defeats No. 1 Roger Federer in 2009

Match Result: 3-6, 7-6 (7-5), 4-6, 7-6 (7-4), 6-2

In 2009, Roger Federer appeared untouchable at the U.S. Open. The five-time defending champion defeated rival Novak Djokovic in one semifinal to set up a championship match against Argentina’s Juan Martin del Potro, who defeated Rafael Nadal in the other. A record sixth straight title was in reach, especially after Federer opened the final by winning its first set.

Del Potro, however would take two tiebreakers over the next three sets, pushing the match into a decisive fifth set.

“I remember the last set and thinking I just have to win. I might never get a chance like this again. I have to win and many times you think it will not happen. Then the moment you win and the dream is here. It is all over. You win and forever more you have won the U.S. Open. It is the most amazing feeling,” said the unlikely Argentine champion. 

Federer should not have felt too disappointed after the loss. You can’t win them all, and by the time he fell to del Potro, Federer already shared the men’s record for the most U.S. Open titles in the Open Era.

  1. No. 2 Mats Wilander defeats No. 1 Ivan Lendl in 1988

Match Result: 6-4, 4-6, 6-3, 5-7, 6-4

World No. 1 Ivan Lendl was the three-time defending U.S. Open champion entering the 1988 tournament, and he would face world No. 2 Mats Wilander in a final that both men reached without any trouble along the way.

The 1988 men’s singles final would go on for four hours and 54 minutes, the longest match in U.S. Open finals history. In a back-and-forth affair, where both men traded sets, Wilander came away with the win to take the world’s No. 1 ranking away from Lendl.

  1. No. 2 John McEnroe defeats No. 1 Bjorn Borg in 1980

Match Result: 7-6 (7-4), 6-1, 6-7 (5-7), 5-7, 6-4

According to The Guardian, the on-court temperature during the 1980 U.S. Open final nearly reached 120 degrees. Tempers were already steamy to begin with, since rivals John McEnroe and Bjorn Borg had just met in an epic five-set Wimbledon final that Borg won.

McEnroe wasn’t going to let Borg have this five-setter despite letting a two-set lead evaporate.

“Bjorn, once again capitalizing on my fatigue and his superior conditioning, started inching his way back into the match. I'm positive he had our Wimbledon match in mind – I know I did. He must have been thinking that I would wilt again, and the king of five-setters would once more prevail,” McEnroe said in his autobiography.

Borg had won 13 straight five-set matches entering the 1980 final, but McEnroe broke him at 3-3 in the fifth set and never looked back. The colorful star who grew up not far from the Open’s home in Queens would go on to win the match ranked here as the best men’s singles final in U.S. Open history.

Parameters of Rankings

Rankings were based on  the length of each championship match, the back-and-forth competitiveness of each match, the hype surrounding each match, and each match’s historical legacy.

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