December 20 brought sad news for the tennis world. Stan Wawrinka, the Swiss star who captured 16 tour titles, including three Grand Slams, announced he will retire from the sport next year. “ONE LAST PUSH,” Wawrinka wrote. “Every book needs an ending. It’s time to write the final chapter of my career as a professional tennis player. 2026 will be my last year on tour.”

The former World No.3 has enjoyed plenty of triumphs over more than two decades on the ATP Tour. He shared the court with legends like Roger Federer, Rafael Nadal, and Novak Djokovic at their peak. Known fondly as “Stan the Man,” he might admit he didn’t always have the best record against the “Big Three,” but he proved himself when it mattered most.

Stan Wawrinka’s first Grand Slam triumph

Novak Djokovic held a commanding 24-6 head-to-head edge over Stan Wawrinka, a rivalry that stretched from 2004 to 2023. Across 30 battles on clay, grass, and hard courts, the numbers tell the story: Djokovic led with 56 sets to Wawrinka’s 26. But as dominant as those stats look, the Swiss always found a way to shake things up when it mattered most.

Wawrinka’s six victories came with a flair for drama, especially on the Grand Slam stage. The 2014 Australian Open quarterfinals was pure theatre. Djokovic, a three-time defending champion, walked in with 14 straight wins over Wawrinka and a 15-2 head-to-head lead. Yet, the Swiss, seeded eighth, produced a stunning 2-6, 6-4, 6-2, 3-6, 9-7 victory after more than four hours of bruising play, snapping Nole’s 25-match rampage at Melbourne Park.

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Still riding that wave, Wawrinka ousted Tomas Berdych in four sets in the semis, then faced Rafael Nadal in the final. Nadal had never lost to him in 12 meetings, but the script flipped that night. Wawrinka beat the Spaniard 6-3, 6-2, 3-6, 6-3 to capture his first Grand Slam trophy, but it wasn’t his first time taking down the 10-time Australian Open champion.

How Wawrinka Conquered Roland Garros

Roland Garros has always tested patience, precision, and power. But for Stan Wawrinka, it became the stage for Grand Slam title No. 2 and another unforgettable run. True to his fearless spirit, he took down not one but two of the Big Three, sending Federer out in the quarter-finals before toppling Djokovic in the final.

Federer, the World No.2 at the time, led their head-to-head 16-2 before that clash on the Paris clay. Yet Wawrinka turned the tables with clean, heavy shots and unstoppable energy, sweeping past his compatriot 6-4, 6-3, 7-6 (7-4). He carried that confidence straight into the semis, where he handled Jo-Wilfried Tsonga to book his spot in the championship match.

Across the net in that final stood World No.1 Djokovic, who had beaten Rafael Nadal in the quarter-finals and Andy Murray in the semis. Many thought the Serb was on track for his first French Open crown. But Wawrinka had other plans.

In a stunning twist, “Stan the Man” roared back to win 4-6, 6-4, 6-3, 6-4, defeating the world No.1 and No.2 in the same tournament to capture the Roland Garros title. And for his third?

Stan Wawrinka dominates the US Open

The Swiss player saved one of his finest acts for New York. In 2016, the Swiss claimed his first US Open crown and third Grand Slam title by once again toppling defending champion Novak Djokovic. The final was a marathon, stretching nearly four hours, with Wawrinka grinding out a 6-7(1), 6-4, 7-5, 6-3 victory.

The No. 3 seed bounced back after a tight opening set, breaking Djokovic late in the next two while saving 14 of 17 break points. His trademark finger-to-temple gesture said it all—the ultimate symbol of focus and fight.

It was the third time Stan Wawrinka had conquered a World No. 1 in a major final. His heavy baseline game and powerful one-handed backhand wore down a weary Djokovic, who battled blisters and fatigue after breezing through earlier rounds. By the end, he no doubt owned the biggest moments under the lights of Arthur Ashe.

That win sealed Wawrinka’s place among the best to challenge the Big Three. Overall in his career, he reached the Nitto ATP Finals four times, with three straight semi-final runs from 2013 to 2015. While most players struggled to crack that elite trio, Wawrinka managed to beat each of them en route to Slam glory, and even took down former World No.1 Andy Murray ten times across their meetings.

Now, the Swiss star prepares to close his incredible career alongside Murray, Federer, and Nadal after his final season in 2026. The question is, can “Stan the Man” summon one last surge and lift a trophy before turning the page to his next chapter?