From McEnroe-Sampras to Nadal-Alcaraz: A gallery of tennis’ cross-generational rivalries

WATCH: A year after his 6-1, 6-2 defeat to Rafael Nadal, Carlos Alcaraz came full circle at the Mutua Madrid Open on Friday with a 6-2, 1-6, 6-3 victory over his childhood idol.

Rafael Nadal versus Carlos Alcaraz represents a tennis moment at once compelling and rare: long-standing genius, face-to-face across the net from precocious and likely future genius.

“I greet you at the beginning of a long career,” were the gracious words with which an American titan of letters, Ralph Waldo Emerson, welcomed a promising young writer, Walt Whitman.  Then again, it was easy for Emerson to be generous.  After all, he never had to return Whitman’s serve.

Here now, five of tennis’ cross-generational signature rivalries, each in their own way showcasing legends in both battle and transition.

Pete Sampras and Roger Federer: Where Else But Centre Court?

Only once did these two smooth-striking all-court greats meet, a round-of-16 Wimbledon battle that took place in 2001. Sampras then was 29 and had won seven titles at SW19. Nearly a decade younger to the day, Federer was in the round of 16 at a major for only the third time.

“From what I’d been told,” Sampras wrote in A Champion’s Mind, the autobiography he collaborated on with Peter Bodo, “he was very talented, but he ran a little hot and cold. I expected to win, but very early in the match I realized that I was up against a kid with a complete game and talent to burn.” For Federer, this was the chance to play one of his childhood idols, that tricky challenge of ignoring the opponent’s resume and instead focusing strictly on the ball. As Federer told journalist Christopher Clarey years later, “You have to work your way through that."

These two had so much in common: height, weight, even the same Wilson Pro Staff racquet. In this last year of Wimbledon’s faster grass, they also rushed the net frequently, Federer serving and volleying 109 times. In the end, the torch had been passed, Federer winning 7-6 (7), 5-7, 6-4, 6-7 (2), 7-5. Perhaps best of all, in the spirit of Emerson, Sampras viewed this transition with class. “I was very impressed,” he said.

Since then, the two have become friends and played several exhibitions and cordial practice matches.

Stefanie Graf and Serena Williams: One End, One Beginning

The year was 1999. A millennium was about to end, a fitting transitional year for two of the greatest players ever to play two scintillating matches. Stefanie Graf had ruled women’s tennis for more than a decade, holding the world number one ranking for a record 377 weeks. But as 1999 began, she was also recovering from a series of injuries and, at the age of 29, uncertain what more she could expect after so many years of rigorous work and competition. In January, in the second round of a WTA event in Sydney, Graf faced 17-year-old Serena Williams. At that point, Williams had only played one full calendar year of pro tennis. But it had been a productive one, Williams’ ranking soaring from 99 at the end of ‘97 to No. 20 a year later.

In Sydney, Graf won a thriller, 6-2, 3-6, 7-5. Two months later, the two met in the finals of Indian Wells. Two weeks prior to that, in Paris, Williams had won her first singles title. Now, in the desert, Graf and Williams played another extremely close match. This time it was Williams’ turn. Rallying from 4-2 down in the third, Williams earned a 6-3, 3-6, 7-5 victory. “It means a lot to me because Steffi is a great champion,” she said. “She has more titles, from what I hear, than any man or lady playing tennis. It's very exciting for me to be able to have this win.”

The balance of 1999 proved eventful for each. In June, the month she turned 30, Graf won the title at Roland Garros—her 22nd and final singles major. In September, the month she turned 18, Williams won the US Open—the first of her current tally of 23 majors.

John McEnroe and Pete Sampras: 'Cool As A Cucumber'

John McEnroe had long hoped for one last lap of brilliance at his hometown major, the US Open. It happened in 1990. Five years after he’d last played a Grand Slam singles final, the 31-year-old McEnroe once again caught fire. Vintage McEnroe came a week prior, when he’d toughed out a five-set win in the round of 16 versus gritty Spaniard Emilio Sanchez. By the tournament’s final Saturday, McEnroe was once again in the semis, keen to reach the finals and earn a fifth US Open title.

Standing in McEnroe’s way was a tranquil Californian, 19-year-old Pete Sampras. Little was known of Sampras at that point, other than that he was regarded as a lively shot maker with tremendous potential. In the previous round, Sampras had beaten Ivan Lendl, a five-set victory that ended Lendl’s streak of eight straight appearances in US Open finals.

But now it was Sampras’ turn to take on tennis’ long-standing rebel, a man who as he’d aged naturally become even more of a fan favorite. Against McEnroe’s aggressive game and a partisan crowd, how would Sampras hold up?

“It was a godsend,” wrote Sampras, “that at some level I really didn’t know what I was doing. I was simply focused on the job at hand, and unaware of the ramifications my success might have.”

He performed the job flawlessly. Point after point, Sampras overpowered McEnroe with an arsenal of shots, including a massive serve, laser-sharp groundstrokes and crisp volleys. Though McEnroe hung in well enough to take the third set, Sampras closed it out smoothly in the fourth, winning the match 6-2, 6-4, 3-6, 6-3. The next day, closing out a fortnight he’d later describe as “a pup, going through a zone,” Sampras beat Andre Agassi in straight sets to become the youngest man in history to win the US Open singles title.

Two weeks later, sitting inside a locker room at his alma mater, Stanford University, McEnroe reflected on what happened that day in New York. “That guy Sampras,” he said, “just cool as a cucumber.”

Jimmy Connors and Andre Agassi: From Las Vegas to New York

Long before they played one another twice in US Open quarterfinal matches, Jimmy Connors and Andre Agassi had met. Throughout the ‘70s, Connors frequently visited Las Vegas, his racquets often strung by a local tennis zealot named Mike Agassi. At least once, Connors hit with a young Andre.

Fast-forward to the 1988 US Open and a quarterfinal match between the 18-year-old Agassi and the 36-year-old Connors. As Agassi wrote in his autobiography, Open, “Before the match I approach him meekly in the locker room and remind him that we once met. In Las Vegas? I was four? You were playing at Caesars Palace? We hit some balls together?”

Connors said he had no memory of this. Nor did he acknowledge that he’d seen Agassi several years later, when Andre had delivered Connors’ freshly strung racquets to him.

And so the stage was set for a generational tussle. The 19,000 spectators packed inside Louis Armstrong Stadium included two notables from Queens—John McEnroe and Donald Trump. In command of the majority of rallies, Agassi won 6-2, 7-6 (6), 6-1. “His will to fight surprised me,” said Agassi. “It was so intense you could feel it.''

Upon learning that Agassi had predicted an easy victory, Connors countered. “I'll remember that the next time we play,” he said. It came at the same stage a year later. This one was closer, but again, Agassi emerged the victor, 6-4 in the fifth.

Those two US Open quarterfinals were the only time Connors and Agassi played one another.

Chris Evert and Tracy Austin: The Shape of Things to Come

Once upon a time there was a highly focused teenaged blonde from a tennis-happy state, armed with superb groundstrokes and even better powers of concentration. The first version was Chris Evert. In 1971, competing in a major for the first time, the 16-year-old Floridian reached the semifinals of the US Open.

Five years later, Evert was number one in the world. At Wimbledon in 1977, she was the defending champion, eager to claim a seventh Grand Slam singles title.

The second version arrived to play Evert in the third round of Wimbledon in 1977. Fourteen-year-old Tracy Austin had sharpened her strong baseline-based game in California. As they entered Centre Court, Evert felt she was about to compete versus a younger version of herself—an awareness that inspired dread. As Evert wrote in Chrissie, the autobiography she collaborated on with Neil Amdur, “If Tracy had been a serve-and-volleyer, someone who gave me a target, I would have been more comfortable. But with the same groundstrokes and determination, I was faced with losing to my own kind. At a tournament like Wimbledon, the media would eat me alive.”

For Austin, it was all quite different. “I felt no pressure,” she wrote in Beyond Center Court, her autobiography, co-written with Christine Brennan. “I had nothing to lose. In fact, I was more nervous about curtsying to the royal box than about playing.”

At 1-1 in the first set, a rarity: Evert fell. She’d later say that the tumble helped her relax. Over the course of 50 minutes, Evert won 6-1, 6-1. Wrote Austin, “My family had been worried I might turn into a zombie and not be able to do anything. On the contrary, I had come out not only intact, but enhanced.”

The other cross-generational rivalries featured here were brief: Federer 1-0 versus Sampras, Graf-Williams 1-1, Sampras 3-0 over McEnroe, Agassi 2-0 against Connors. But Evert-Austin was far more extensive, with Austin in the end winning nine of their 17 matches.