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Jannik Sinner holds one advantage as he bids to complete tennis feat which has never been managed before

Photo by Daniel Kopatsch/Getty Images
Photo by Daniel Kopatsch/Getty Images
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Jannik Sinner continued his remarkable 2026 season on the ATP Tour with a title defence at this year’s Wimbledon Championships.

Sinner went back-to-back at the All England Club to hoist his fifth Grand Slam trophy, just two shy of his biggest rival, Carlos Alcaraz.

The triumph was the first at a major this season for the Italian, who had lost in the semifinals of the Australian Open and the second round of Roland Garros.

Who has more Wimbledon titles by 2036 between Jannik Sinner and Carlos Alcaraz?

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Jannik Sinner v Carlos Alcaraz Wimbledon question graphic

While the Grand Slam season has not been entirely successful for Sinner, the world number one has completely dominated at ATP Masters 1000 level.

He has won every Masters event of the season so far, emerging victorious in Indian Wells, Miami, Monte-Carlo, Madrid and Rome.

Now, ahead of the sixth Masters 1000 competition of the year in Montreal, Sinner will resume his bid to achieve a feat nobody has ever managed in tennis history.

Jannik Sinner holds the Italian Open title in 2026.
Photo by Filippo MONTEFORTE / AFP via Getty Images

Jannik Sinner’s quest to make history continues in Canada

By winning the Italian Open, Sinner became just the second man to complete the Career Golden Masters, the name given to the achievement of winning all nine Masters 1000 tournaments at least once.

He joined Novak Djokovic in the exclusive list of players to do it, with the Serb completing the set at the Cincinnati Open in 2018.

But no man has ever won all nine ATP Masters 1000 tournaments in a calendar season, a record Sinner is on his way to clinch.

Sinner has just four tournaments left to win to make history: The Canadian Open, the Cincinnati Open, the Shanghai Masters and the Paris Masters, all of which are played on his statistically-favoured surface of hard court.

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Jannik Sinner prove me wrong graphic

An issue facing many players in pursuit of winning the Canadian Open in years gone by is the short time period between the Masters tournament and the conclusion of Wimbledon.

This year, however, the gap between Wimbledon and the Canadian Open has been extended by a week, giving Sinner extra time to recover after his Wimbledon campaign.

Not only that, but Sinner will be relatively fresh as it is, having not played any tour-level events between Roland Garros and Wimbledon.

With Alcaraz still out with injury and Djokovic playing a limited schedule, Sinner may never get a better opportunity to complete the historic accomplishment.

Jannik Sinner looks on in London.
Photo by Clive Brunskill/Getty Images

Jannik Sinner has chance to match three tennis greats this summer

If Sinner wins both Canada and Cincinnati, he will have the chance to complete another incredible feat only three others have ever managed.

Patrick Rafter, Andy Roddick and Rafael Nadal are the only three players to have won the Canadian Open, the Cincinnati Open and the US Open in the same year.

Rafter did it in 1998, Roddick in 2003 and Nadal was the most recent to join the club, winning all three tournaments in 2013.

Sinner won both the Cincinnati Open and the US Open in 2024, but was knocked out in the quarterfinals of the Canadian Open that season.