Stan Wawrinka continues to turn back the clock. Just weeks after an emotional Australian Open farewell, the Swiss veteran added another historic chapter to his farewell season at the ATP 500 Rotterdam.

After a hard-fought third-round exit to Taylor Fritz in Melbourne and a Round of 16 appearance at the Open Occitanie, Wawrinka has now reached the fourth round in Rotterdam – marking back-to-back deep runs on tour. But this latest victory was about far more than just progression. The 40-year-old defeated 17-year-old Dutch lucky loser Thijs Boogaard 6-3, 6-4 in a first-round clash that spanned generations. The 23 years and 100 days separating the two players now stands as the second-biggest age gap in a tour-level match since 1990.

Only one match tops it – Dominic Thiem’s 2011 Vienna victory over 44-year-old Thomas Muster when the Austrian was just 18. That gap exceeded Wawrinka-Boogaard by two years and eight months.

While the scoreline itself may not go down as a classic, the context certainly will. Wawrinka, who first won the Rotterdam title in 2015, became part of another unique statistical milestone in ATP history. It’s a staggering thought that the three-time Grand Slam champion has now faced players born in entirely different eras, once competing against Fabrice Santoro (born in 1972) and now against Boogaard, born in 2008. That timeline alone encapsulates the longevity of Wawrinka’s career.

Even more impressively, the Swiss star is set to return to the Top 100 for the first time in 18 months when the rankings update on Monday – an achievement few would have predicted amid his injury struggles over the past few years.

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Stan Wawrinka’s resurgence had already made headlines in Melbourne, where he became the oldest man since Ken Rosewall to reach the third round of the Australian Open. Now, Rotterdam has provided yet another reminder of its enduring competitiveness. Next up is a stern test against top seed and two-time defending finalist Alex de Minaur, who leads their head-to-head 1-0. Yet Wawrinka remains unfazed.

Stan Wawrinka shares thoughts about his next opponent in Rotterdam

“He’s a tough player,” Wawrinka said about the Australian. “Especially in these conditions, it’s going to be difficult to generate something. But I’m looking forward to the challenge. I’ve been playing some good matches against top players, so I’m always trying to push myself.”
At nearly 40, Stan Wawrinka isn’t just competing – he’s rewriting longevity records. And in a sport constantly chasing the next big thing, the Swiss veteran just proved that experience still has its place on the biggest stages.

And perhaps that’s what makes his latest milestone in Rotterdam even more poignant – it’s not just about records anymore; it’s about legacy in motion. Back in December 2025, Stan Wawrinka officially broke his silence on retirement, confirming that 2026 would be his final season after 23 remarkable years on Tour. With 16 singles titles, including three Grand Slam crowns, an Olympic gold medal in doubles (Beijing 2008), and a career-high ranking of World No. 3 in January 2014, the Swiss icon decided it was time for “one last push.”

Those three words carried immense weight. “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… I still want to push my limits and finish this journey on the best note possible. I still have dreams in this sport,” Wawrinka wrote in his emotional Instagram post.

But interestingly, not everyone is convinced that 2026 will truly be the end. Former World No. 8 John Isner recently floated a bold theory on the Nothing Major Show, suggesting Wawrinka could reconsider retirement if results continue trending upward.

“I have got a hot take on Stan. I think he reconsiders retirement,” Isner said. “If he is 60 to 70 in the race at that time, and he is clearly in the Australian Open on his own, at approaching 41, I think he reconsiders.”

Sam Querrey echoed the sentiment, adding, “I am with you. I don’t even think he reconsiders. I think he just plays 2027.” Looking at Stan Wawrinka’s start in 2026, the speculation doesn’t feel entirely unrealistic. What are your thoughts on this, though? Share with us in the comment box.