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The Grand Slam champion that Pete Sampras said was his toughest-ever opponent after retirement

Photo by Simon Bruty/Anychance/Getty Images
Photo by Simon Bruty/Anychance/Getty Images
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Pete Sampras enjoyed a legendary tennis career that many believed would never be topped.

American tennis may have experienced somewhat of a lull over recent years, but there was once a time when the nation produced the very best players on the ATP Tour.

Sampras was most certainly one of them, winning a then-record 14 Grand Slam men’s singles titles during his 14-year career.

The now 53-year-old won his final Major title at the US Open in 2002, playing his last professional match on Arthur Ashe Stadium.

Sampras kisses the trophy
Photo by Al Bello/Getty Images

The American enjoyed several legendary rivalries on the ATP Tour, including one with Pat Rafter, who he took on 16 times, winning 12 of those encounters.

However, looking back on his career in 2007, Sampras admitted who his toughest-ever opponent was.

Pete Sampras said Andre Agassi was his toughest-ever opponent after retirement

In a 2007 interview with the Guardian, Sampras was asked to pick his toughest opponent during his 14-year career.

Andre Agassi,” he said.

Arthur Ashe Kids' Day Tennis Festival
Photo by Theo Wargo/Getty Images

“We had contrasting styles and he had that extra gear, if you made a mistake, then you knew it was game over.

“I also like to think that I made him realise that how you played was more important than your image.”

Sampras played Agassi in his final-ever match at the US Open in 2002, beating him 6-3, 6-4, 5-7, 6-4.

The American went on to reveal what he made sure to do to Agassi after he retired from tennis.

“When he retired last year, I thought it was important to reach out to him so I sent him a few text messages,” he said.

“It would have been a shame for us not to be in contact just because we were both no longer playing.

“Now we’re retired and bringing up young families, we joke about how much we finally have in common.”

Sampras was also asked to pick a favorite of his 762 wins, and couldn’t help but circle back to his win over Agassi in 2002.

US Open-Mens Final
Photo by Ezra Shaw/Getty Images

“Possibly Wimbledon in 2000, when I completed a record seventh win and my parents were there for the first time,” he said.

“Then there was the US Open victory in 2002.

“I hadn’t won a Grand Slam in two years and was really down, that was a great way to go out.”

Who won the head-to-head between Pete Sampras and Andre Agassi?

Sampras thought that Agassi was his toughest opponent, but who got the better of their encounters on the ATP Tour?

The pair played one another 34 times in total, with Sampras edging the head-to-head 20-14.

Sampras also looked to have the advantage over his rival at the Grand Slam level.

MatchWinnerLoserScore
2002 US Open – FPete SamprasAndre Agassi6-3, 6-4, 5-7, 6-4
2001 US Open – QFPete SamprasAndre Agassi6-7, 7-6, 7-6, 7-6
2000 Australian Open – SFAndre AgassiPete Sampras6-4, 3-6, 6-7, 7-6, 6-1
1999 Wimbledon – FPete SamprasAndre Agassi6-3, 6-4, 7-5
1995 US Open – FPete SamprasAndre Agassi6-4, 6-3, 4-6, 7-5
1995 Australian Open – FAndre AgassiPete Sampras4-6, 6-1, 7-6, 6-4
1993 Wimbledon – QFPete SamprasAndre Agassi6-2, 6-2, 3-6, 3-6, 6-4
1992 French Open – QFAndre AgassiPete Sampras7-6, 6-2, 6-1
1990 US Open – FPete SamprasAndre Agassi6-4, 6-3, 6-2
Pete Sampras and Andre Agassi’s head-to-head record at Grand Slam tournaments

The 53-year-old won six of his nine meetings with Agassi at Major tournaments, taking him down in four Grand Slam finals.

12 years before he beat him in his final-ever match, Sampras secured his first Grand Slam win against Agassi at the US Open.

Will any current American ATP stars match Pete Sampras and Andre Agassi’s tennis achievements?

Sampras and Agassi combined for 22 Major titles during their time on the ATP Tour.

Since the pair last won a Grand Slam title, only one American male has picked up a Major, when Andy Roddick took home the US Open in 2003.

The United States has waited 22 years for a Major winner on the men’s side, but the current crop of American talent could provide their best chance at success in several years.

There are currently eight American players ranked inside the world’s top 50, some of which have come very close to ending the 22-year drought.

US RankATP RankNameBest Grand Slam resultMost recent Grand Slam result
14Taylor FritzF – 2024 US Open3R – 2025 Australian Open
29Tommy PaulSF – 2023 Australian OpenQF – 2025 Australian Open
314Ben SheltonSF – 2023 US Open, 2025 Australian OpenSF – 2025 Australian Open
418Frances TiafoeSF – 2022 US Open, 2024 US Open2R – 2025 Australian Open
522Sebastian KordaQF – 2023 Australian Open2R – 2025 Australian Open
636Alex Michelsen4R – 2025 Australian Open4R – 2025 Australian Open
741Brandon Nakashima4R – 2022 Wimbledon, 2024 US Open1R – 2025 Australian Open
843Marcos Giron3R – 2021 French Open, 2023 French Open, 2025 Australian Open3R – 2025 Australian Open
American ATP players ranked in the top 50

Fritz reached the final of the US Open in 2024, becoming the first American Major finalist since Roddick, as he came up short against Jannik Sinner in the final.

Tommy Paul, who recently made his top-ten debut, and Ben Shelton who reached a second-career Major final earlier this month, could also challenge for a Grand Slam title in the near future, as they continue to shine against the elite players on tour.

Only time will tell if Fritz, Paul, Shelton, or any other American ATP stars can win a Major title, but they’ll all no doubt be looking to make their mark at the French Open, which begins on Sunday, May 25.