Wondering what the Tournament of Champions is, and how we got here? Read more about our 50th Anniversary Celebration and get caught up on all the matches so far.

These two countrymen, fellow Hall-of-Famers, and occasional doubles partners overlapped long enough to face each other three times in 1990 and 1991. A very young Sampras was on the way up, and an over-30 McEnroe was on the way down; the combination didn’t work out so well for Johnny Mac, who managed to win just one set in those three matches. It was clear, when a 19-year-old Sampras used his pistol serve to blast McEnroe off the court at Flushing Meadows in 1990, that U.S. tennis had a new sheriff—no one had seen a display of power like that before.

Would the result be the same if the two were to meet in their primes, on three different surfaces? One player who faced both men, Tim Mayotte, thinks the match would be closer, but the outcome would be the same. “John didn’t return well enough to get at Pete’s serve, the most devastating shot I ever faced,” Mayotte says. “Pete would have a tough time breaking John as his backhand was relatively weak, but late in sets and breakers you got to go with Pete.”

McEnroe, who reached a French Open final, might have the edge on clay, and he would come up with a few trademark moments of genius. But over three sets and three surfaces, “Sampras prevails,” Leif Shiras believes, “because he has the biggest and best shots on the court. Mac never breaks serve, but is warned for arguing with an umpire on a call in the third.”

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Quarterfinal: (3) Pete Sampras vs. (13) John McEnroe

Quarterfinal: (3) Pete Sampras vs. (13) John McEnroe