(Left-right) Björn Borg wears Rolex Day-Date; Roger Federer wears Rolex Sky-Dweller; Stefan Edberg wears Rolex Oyster Perpetual Datejust 41. Images: (of athletes) Getty Images; (of watches) courtesy of Rolex

WHEN A BROADCASTING camera zooms in on a player about to set the ball into play, yes, you admire their form, waiting for them to strike with bated breath. But in the few seconds before physics ensues, you also notice their watch. And for a sport that makes superstars out of its players – and one that’s historically been for (both played by and enjoyed over) the upper-middle-class – some serious timepieces have been spotted on the very best stars throughout the years. This makes sense given the price tag when you see how many zeros are in the prize money, but only the finest and most charismatic exponents have worn the best watches. In the shared pursuit of artistry and and excellence, it’s only ever been Rolex.

Here, Esquire looks back at the brand’s history of partnerships with tennis’ most iconic players, and, indeed, what their timepieces reveal about their time at the top. As we’ll see with Roger Federer, the Swiss master with the Swiss master watchmaker is a natural link-up.

Björn Borg – Rolex Day-Date

Bjorn Borg wears Rolex Date-Date
Bjorn Borg wears Rolex Date-Date

The Swedish baseliner, an 11-time Grand-Slam champion, ruled tennis from 1975-80, his combination of heavy topspin, cat-like movement and icy temperament proving unbeatable on both the Roland-Garros clay and the grass of Wimbledon. “When I look at my Rolex, I think back to the success I had on the court,” Borg says. “It’s a Day-Date that came out in 1956, the year I was born, so it’s the perfect watch for me.”

Stefan Edberg – Rolex Oyster Perpetual Datejust 41

Stefan Edberg wears Rolex Oyster Perpetual Datejust 41

When just about everyone else in pro tennis was glued to the baseline, the unflappable Swede kept on serve and volleying – and to great effect: he won six Grand Slam titles between 1985-92. He later coached Roger Federer between 2013-15, refining the maestro’s net game and contributing to his late-career resurgence. Edberg’s other link with greatness? “I feel privileged to be a Rolex Testimonee and to be part of one of the most prestigious companies in the world.”

Jim Courier – Rolex GMT-Master II

Jim Courier wear Rolex GMT-Master II

In the early ’90s, even with Pete Sampras and Andre Agassi circling, Floridian Jim Courier was The Man, claiming four major titles (two French, two Australian Opens) between 1991-93. An uber-intense competitor, he went on to become a superb tennis commentator. In Rolex, Courier sees a kindred spirit: “They’re committed to their craft,” he says, “committed to the perfection of their timepieces.”

Rod Laver – Rolex Datejust 36

Rod Laver wears Rolex Datejust 36

The tennis legend known as ‘Rocket Rod’ did something no member of the modern-day Big Three could manage: he captured the Grand Slam (winning all four major tournaments in the same year). What’s more, he did it twice – in 1962 and ’69. “Getting a Rolex was the crowning moment of my career,” Laver says. “It’s the reputation, the quality. It’s the number-one watch in the world – and one you can have all your life.”

Pat Rafter – Rolex Yacht-Master

Pat Rafter wears Rolex Yacht Master

Like Edberg, the Mount Isa-born Rafter bucked the trends of ’90s tennis, taking on the baseliners with a superlative serve-and-volley game that yielded consecutive US Open titles in 1997-98, as well as, briefly, the world No. 1 ranking. Some of his battles with stylistic opposite Andre Agassi were classics. Like all pros, Rafter had to overcome numerous setbacks while on the tour, including the theft of a beloved Rolex from the locker room at a ’90s US Open.

Roger Federer – Rolex Sky-Dweller

Roger Federer wears Rolex Sky-Dweller

The Swiss master has been surpassed for major titles won, but has anyone ever played the game as beautifully? Tennis goes on, but with a Federer-sized hole in its heart. “The Rolex Sky-Dweller I received after winning the Australian Open in 2017 is the watch which holds the most sentimental value to me,” Federer says. “It has a butterfly engraving because I referred to having butterflies before the final, so it was a special message from the Rolex family.”


This story appears in the December/January 2024-25 ‘Summer of Tennis’ special issue of Esquire Australia, on sale now. Find out where to buy the issue here.

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