The VIP stand: From Novak Djokovic to Usher, who is ringside in Milano Cortina 2026?

When the Winter Olympics rolled into Milano Cortina 2026, it was not only the athletes competing in the greatest theatre of sport that demanded attention. The who's who of international sport, music, fashion and film turned their gaze to the best of the best on ice and snow.

Two years after shining at the Summer Olympics, G.O.A.Ts of their respective trades, such as Novak Djokovic and Simone Biles turned heads on the sidelines.

Serbian tennis legend and Olympic champion Djokovic, fresh off his run to the Australian Open final, was spotted with his wife Jelena, watching the figure skating team event.

Djokovic watched in amazement as U.S. superstar and ‘Quad God’ Ilia Malinin mesmerised the audience during his routine during the team event.

In a game-recognises-game moment, Djokovic gave Malinin a standing ovation after his free skate, which clinched the gold for Team USA.

"I did see Djokovic. It's so unreal," Malinin said after his skate.

"I heard that after I landed my backflip, he had his hands over his head. That's incredible. That's a once-in-a-lifetime moment: Seeing a famous tennis player watching my performance. I'm absolutely blown away."

The red-carpet gala at Milan's iconic La Scala opera house ahead of the Opening Ceremony attracted other global icons such as five-time Olympic speed skating gold medallist Bonnie Blair, Donatella Versace, Usher, and Stanley Tucci.

The figure skating proved to be a popular destination for some of our famous fans, with seven-time Olympic artistic gymnastics gold medallist Biles attending both the men’s and women’s events.

“There is a little bit of familiarity around [the sport], but I would never do it on ice,” Biles said during an in-arena interview on Friday.

“I give them all the props, I’m rooting for them, I’m praying for them. I’m just super excited to watch today.”

Chief among past legends from past Winter Olympic Games showing support to the current stars was snowboarding G.O.A.T Shaun White.

The three-time Olympian is in Milano Cortina 2026 working for U.S. broadcaster NBC and watching the action on the superpipe with interest.

White said he was excited to watch the action from the sidelines with a keen eye on two of the current superstars. “Eileen Gu, she’s a legend,” White said. “Her dedication to training, her ability in the halfpipe. And Chloe [Kim] is in a league of her own.”

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