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As a player, Darren Cahill won two singles titles and 13 doubles titles, achieving career-high rankings of No. 22 in singles and No. 10 in doubles.

Following his retirement, Cahill has gone on to coach some of the game’s greatest players—from Lleyton Hewitt and Andre Agassi to Simona Halep and, most recently, current ATP World No. 1 Jannik Sinner.

Just a week after the thrilling Roland-Garros men’s final, Cahill takes us behind the scenes of that legendary match between Sinner and Carlos Alcaraz, sharing what it was like in the locker room after the loss.

He also discusses how coaching and playing styles have evolved, Sinner’s remarkable self-awareness, why the 23-year-old is eager to experiment on court, and how the legacy of the ‘Big 3’ continues to shape the next generation of tennis stars.

JW gets Cahill to open up about his family’s coaching legacy back home in Australia—and you won’t want to miss the story of how he and Andre prepared for a match against Andy, even if their meeting was short-lived.

The WTA returned to Queen’s Club this week and delivered its long-awaited champion.

Tatjana Maria, a 37-year-old mother of two, sliced her way to her first WTA 500 title and became the first woman to win a singles title at Queen’s Club in 52 years. She also made history as the oldest player to win a WTA 500 event, just two months shy of her 38th birthday.

The German qualifier carved through a loaded draw, consecutively defeating four top-20 players: Karolina Muchova, Elena Rybakina, Madison Keys, and Amanda Anisimova in the final.

Maria says she plans to play as many grass-court matches as possible before Wimbledon, where she made the semifinals in 2022. She also told WTAtennis.com her long-term goal is to one day play doubles with her daughter Charlotte.

“To be honest, I feel great on the court. I feel great body-wise,” Maria said. “And I always say, as long as I feel good and I don’t have pain, I can keep going.”

Andy called it a “superhero week”, praised Maria’s tactical precision, and gave a shoutout to all the parents competing on tour.

More history was made during the first week of the grass-court season.

At the Libema Open, Elise Mertens captured her first title on grass—and the 10th WTA singles trophy of her career—after saving 11 match points in the semifinals, the most saved by any player in a tour-level main draw this decade.

It was a homecoming of sorts, as ’s-Hertogenbosch, Netherlands is roughly an hour and a half drive from her hometown of Leuven, Belgium.

With the win, Mertens now has titles on all major playing surfaces and lifted her second trophy of 2025.

It was also a week of firsts for Gabriel Diallo. The Canadian not only earned his first tour-level win on grass—he rattled off four more to claim his first ATP title on Sunday.

Diallo defeated his close friend and doubles partner, Zizou Bergs, in the final and jumped 11 spots to a career-high ranking of World No. 44. He also upset top-25 ranked players Karen Khachanov and Ugo Humbert along the way.

The 23-year-old became just the fourth Canadian to win an ATP singles title this century. While he dashed Bergs’ hopes of a first title, the duo plans to team up for the Wimbledon doubles draw.

The grass-court swing arrived at just the right time for top American Taylor Fritz, following a disappointing clay season.

Fritz didn’t drop a set or lose serve en route to the Stuttgart title, defeating Alexander Zverev in the final—his fifth consecutive win over the German—and climbed back to World No. 4.

It marks his first title of 2025, the ninth of his career, and his fourth on grass.

Elsewhere at the Boss Open, fellow American Ben Shelton reached the semifinals and broke into the ATP Top 10 for the first time. With Fritz at No. 4 and Tommy Paul at No. 8, it’s the first time since 2006 that three American men are ranked inside the Top 10.

German 17-year-old Justin Engel also made headlines, becoming the youngest player in 40 years to reach the quarterfinals of an ATP grass-court tournament. He’s now the second youngest player since 1990, the youngest since Rafa Nadal, to win tour-level matches on grass, clay, and hard courts.

Andy reminds us not to “sleep on Taylor Fritz on grass” and weighs in on Shelton’s “steady cadence” as he continues his rise.

Have You Been Keeping Up With Served With Andy Roddick?

Andy makes his case for tennis players being the best athletes in the world. Do you agree or disagree?

• Swinging Into Pickle: PXG, known for its premium golf gear, has officially entered the pickleball equipment market with the launch of two high-performance paddles

• One Association: The International Association of Pickleball Facilities is rebranding as the International Association of Pickleball and Padel Facilities (IAPPF) as it expands into the booming sport of padel

• Game On, Ireland: Ben Keohane’s Padel 100 has secured a €5 million investment to install 100 new padel courts across Ireland by December, aiming to grow the sport beyond elite clubs and capitalize on celebrity-driven interest

• Crossover Chaos: Iga Swiatek and Daniil Medvedev teamed up to take on two professional padel players in a lighthearted yet challenging Tecnifibre exhibition that’s a must-watch

98% of you said ‘yes’! We can’t wait either. Only two more weeks…