Top 5 Oldest Men's Singles Grand Slam Winners in Tennis History

In every sport, athletes are expected to give it their all. Reaching the top takes years of relentless training, discipline, and dedication. But even after achieving peak performance, time eventually catches up — age often chips away at speed, strength, and stamina.

Tennis, in particular, is a grueling sport. It demands not only physical fitness — including agility, endurance, and power — but also sharp mental focus. Matches are played across different surfaces and under constantly changing conditions, putting players at continuous risk of injury. As a result, most players find it tough to maintain their level as they grow older.

Yet, a rare few have managed to defy the odds — and time — to stay competitive at the highest level. These exceptional athletes have not only continued playing well into their later years but have also claimed Grand Slam titles when many had written them off.

With that in mind, 

5. Andres Gimeno – 34 years 305 days

Andrés Gimeno is one of the many Spanish greats to have left a lasting mark on tennis. The Catalan carved out a unique place in history by becoming the oldest first-time Grand Slam champion when he won the French Open in 1972.

Gimeno enjoyed a relatively smooth start to the tournament, breezing through the opening two rounds. However, things got tougher in the third round, where he was pushed to five sets by American Clark Graebner.

From the quarterfinals onward, every match was a battle. Despite often dominating a set, Gimeno had a tendency to unexpectedly drop the next, adding drama to his run. But as is often the case with Spanish players at Roland Garros, his connection to the clay proved key.

At 34, Gimeno finally captured his first—and only—Grand Slam title. Unfortunately, his career was cut short just a year later when a meniscus injury forced him into retirement. Still, his 1972 triumph remains a special chapter in tennis history.

4. Rafael Nadal – 36 years 2 days

If there’s one name that consistently echoes through the record books of tennis, it’s Rafael Nadal. Following in the footsteps of Spanish legends like Manuel Santana, Andrés Gimeno, and Carlos Moyá, Nadal didn’t just walk the path—they helped carve it, and he turned it into his own legacy.

On his day, Nadal is virtually unstoppable—especially on clay, where he has long been the undisputed king. Fittingly, his most recent Grand Slam victory came on the very surface he has ruled for years: the red clay of Roland Garros.

In the 2022 French Open, Nadal was handed a brutal draw. He had to face the World No. 1 and defending champion, Novak Djokovic, in the quarterfinals. But Nadal rose to the occasion, outplaying Djokovic in a gripping match. On his 36th birthday, he got an unexpected gift when Alexander Zverev retired due to injury in the semifinals after a fierce contest.

In the final, Nadal faced rising star Casper Ruud and delivered a masterclass, winning in straight sets. With that victory, he claimed a record-extending 14th French Open title and his 22nd Grand Slam overall—a historic achievement that further cemented his legendary status in the sport.

3. Novak Djokovic – 36 years 111 days

Novak Djokovic broke Rafael Nadal’s record of 22 Grand Slam titles, proving once again that—like a fine wine—he only gets better with age. He matched Nadal’s tally at the 2023 Australian Open, then surpassed it with a historic win at the French Open later that year.

Although he fell short at Wimbledon, losing a thrilling final to Carlos Alcaraz, Djokovic bounced back in style. He claimed the US Open title by defeating Daniil Medvedev in straight sets, rarely looking troubled throughout the tournament. The biggest scare came in the third round, where fellow Serbian Laslo Djere pushed him to five sets after taking the first two—a rare sight, but Djokovic quickly regained control.

Now 38, it’s been two years since his last Grand Slam win. Still, with 24 titles under his belt, Djokovic remains hungry for more. He’s eyeing Grand Slam No. 25—and the chance to stand alone at the very top of tennis history.

2. Roger Federer – 36 years 173 days

Roger Federer has always been the epitome of class on a tennis court. From his early battles against legends like Pete Sampras to his dominance over his own generation, the Swiss maestro was always a joy to watch. His final Grand Slam triumph came at the 2018 Australian Open, where he entered as the defending champion.

Federer was in top form throughout the tournament, breezing through his matches with trademark elegance. With Rafael Nadal forced to withdraw in the quarterfinals, the path seemed clear, and most fans and pundits had their money on Federer.

In the final, he faced Marin Čilić, who put up a fierce fight. The Croatian pushed the match to five sets, but in the end, Federer’s experience and brilliance shone through. He clinched the title, making history at 36 years and 173 days old — becoming the oldest player since the turn of the millennium to win a Grand Slam.

1. Ken Rosewall – 37 years 54 days

1972 was a landmark year in tennis, with the formation of the ATP after a long conflict between the ILTF and WCT. The year began with controversy as the Australian Open was moved to Christmas weekend to avoid a ban on WCT players. But the timing meant many top players skipped the event, and only eight non-Australians were in the draw.

Defending champion Ken Rosewall entered as the favorite. In the final, he faced Mal Anderson, who had earlier upset top seed John Newcombe in the quarterfinals. But Rosewall proved too strong, winning in straight sets. It was his eighth Grand Slam title and his fourth at his home turf.

Cover Credits - Sky Sports