But before carving out a career in the media, John McEnroe made his name as one of the best tennis players of all time.

He claimed seven Grand Slam titles and is regarded as one of the best serve and volley players in the game’s history, but there was one who he always struggled to play his best against.

John McEnroe names the player he found toughest to face

McEnroe faced the likes of Bjorn Borg, Jimmy Connors, Boris Becker and Ivan Lendl, some of the game’s best players.

The 66-year-old achieved varying levels of success against these players, but there was one player in particular that he could not beat.

Pete Sampras emerged as a top contender at the start of the 1990s, when he turned 19 years of age, while McEnroe had just entered his thirties, and he was overwhelmed by what his oppo brought to the court.

“I had the opportunity to face a lot of great players,” McEnroe said back in 2022 for WIRED’s YouTube channel. “Won and lost. Did my share of losing against a lot of them. Bjorn Borg obviously was my greatest rival.

“Jimmy Connors was an incredible competitor along the likes of Rafael Nadal, the effort he gave was very intimidating. My toughest opponent I ever played though, at the end of my career unfortunately, and the beginning of his – his name was Pete Sampras.

“It felt like I just had the racket taken out of my hands, it didn’t matter what I did almost, he served so big and was hitting the ball so hard that I wasn’t able to do my thing. He took me out of my game and I wasn’t moving as well as I was early in my career, so that made it a lot worse.”

What was John McEnroe’s head-to-head against Pete Sampras?

McEnroe played Samapras three times before his singles career came to an end in 1994.

Their first meeting came at the 1990 Canadian Masters in the quarter-finals, and Sampras claimed a 7-6, 4-6, 6-3 victory.

Just weeks later, the American duo played in the US Open semi-finals, and once again Sampras won in four sets to advance to the final before winning his first Grand Slam title.

McEnroe and Sampras’ third and final match came at the ATP Tour event in Philadelphia for a spot in the final.

He claimed a 6-2 6-4 victory to reach the final and McEnroe ended his illustrious career without being able to register a win over Sampras.