Wimbledon's most iconic celebrity moments from Cliff Richard's impromptu concert to Princess Diana's fashion parade and David Beckham catching a ball

The annual  Championships is making its grand return to SW19 on Monday, with some of the biggest stars set to appear on Centre Court.

Guests from around the world will flock to the All England Lawn Tennis and Croquet Club from June 14 to July 12.

Yet while the focus is supposed to be on the tennis matches, often it's the celebrity attendees who steal the show. 

The sporting occasion is rooted with history and is home to some of the best Centre Court fashion. 

Indeed, the annual star-studded affair has seen plenty of iconic times over the years, from 's fashion parade to 's impromptu concert and  casually catching a ball.

Now, as Wimbledon prepares for its 139th edition, the Daily Mail takes a look back at some of the best celebrity moments. 

Princess Diana's fashion parade

Princess Diana was the original IT Girl of Wimbledon, showcasing her signature style in the Royal Box.

Even before her marriage to in 1981, Diana was a frequent contender with her sister Lady Sarah Spencer. 

Diana often opted for a flowing summer dress or structured skirt suit in seasonal summer shades.

Beginning in the 1980s, the late Princess Of Wales set the standard for Wimbledon fashion - with stars still to this day being influenced by her regal looks. 

Sir Cliff Richard's surprise gig 

Sir Cliff performed an impromptu 20 minute gig during a rained-off men's quarter final back in 1966. 

'It was all totally unplanned, it was a wonderful accident and I'm happy to have been a part of it', he later told the Guardian. 

He was doing an interview with Radio Wimbledon in the Royal Box when he was asked to sing by the club secretary. 

He started with ‘Summer Holiday’, saying to the crowd, ‘I never thought I’d actually play on Centre Court’. 

Cliff performed six songs for a total of 20 minutes to an audience that included Prince and Princess Michael of Kent and Joanna Lumley.

His set included a version of ‘Singin’ in the Rain’, backed by tennis stars such as Martina Navratilova and Pam Shriver. 

‘How could anyone have ever dreamed up a backing group like this?’ he said to a huge round of applause. 

And as he launched into ‘Congratulations’, with the crowd clapping to every beat, the covers were rolled back and play was restored. 

David Beckham's magic touch

In true nonchalant Beckham style, David showed off his quick flexes in 2015 when he caught a wayward ball from the Royal Box.

The former England footballer sparked a round of applause from the crowd after the tennis ball bounced off a line judge's chair and into the Royal Box where he managed to grab it. 

He smiled and raised his arm to acknowledge the cheers after throwing it back into Centre Court from his prime seat, beside his mother Sandra, during their day at the All England Club. 

It all gets a bit too much for Talulah Riley 

Celebrities' dramatic reactions during the match are often caught on camera.

Talulah Riley took to Instagram in 2022 to joke about photos taken of herself and boyfriend  as they watched all the tennis action together.

The St. Trinians star shared an hilarious selection of shots - which showed her yawning, seemingly sleeping and generally putting on an extremely animated display with her actor beau - and made light of her antics.

Talulah wrote in a lengthy caption alongside her upload: 'Have been in giggles for days at these candid shots from @wimbledon. 

'We posed very demurely at the @champagnelanson sign — Thank you, Lanson, for having us! And for feeding us all day long (lamb wellington, strawberries-and-cream, afternoon tea, pick-and-mix to take to court, lots of Lanson for Thomas. Yum.)

'But didn't quite realise how visible we were (all day long…) while watching the tennis. 

'I usually describe myself as ''stoic,'' but having seen these images I'm quite sure I can no longer make that claim…

'In a previous era, these might also be titled: ''Why not to take your girlfriend to a sporting event.''

'I honestly don't know why I'm yawning/appear to be asleep in a lot of these shots. I was genuinely riveted by the matches.

'And thank you again, @champagnelanson for having us and for your very generous hospitality.

'It was also lovely to have a mini @pistol reunion with @emmajappleton. And thank you @mrselfportrait for the loan of such a pretty dress. I really loved it.'

Hugh Grant falls asleep

The excitement of the Wimbledon quarter-finals was too much for Hugh Grant last year, as he appeared to fall asleep while on camera in the Royal Box.

Footage aired on the BBC showed Hugh nodding off mere minutes after chatting to Queen Camilla, having arrived for the match with his wife Anna. 

Fans were left in hysterics as they spotted the moment during the channel's Wimbledon coverage, as it was shared on X with the caption: 'It's all got a bit too much for Hugh Grant.'

Posts on X included: 'Hugh Grant asleep at the tennis lol;'

'Now why Hugh Grant look like he's asleep at Wimbledon; Someone wake up Hugh Grant, dude is out cold.'

In 2021, Hugh yet again looked to be ready for bed as he watched a tennis match alongside wife Anna Elisabet Eberstein.

Sienna Miller's awkward moment

 is often one for catching the headlines with her stylish ensembles and

So it didn't seem particularly strange when Sienna and Oli shared a steamy smooch in the stands in 2022. 

However, the moment occurred just as her ex Tom Sturridge kissed his new love interest Alexa Chung while sitting just rows away watching centre court.

Sienna split from Tom, the father of her daughter, in 2015 after four years together. 

She welcomed her third child in May, her second with Oli. They also had a daughter in January 2024. 

While many might expect bumping into an ex and his new partner would be awkward, Sienna proved there was no hard feelings as she caught up with the pair 

The friendly foursome were even seen posing for a selfie together as a beaming Sienna snapped away on her phone. 

Ariana Grande's surprise appearance

 made a star-studded appearance as she cuddled up to Wicked co-star and pal Jonathan Bailey  in 2023.

The singer beamed as she shared a joke with the Bridgerton star while watching Serbia's Novak Djokovic take on Spain's z in the Men's Final from their VIP seats. 

Ariana cut a stylish figure a grey knitted short sleeved maxi dress from Ralph Lauren which she teamed with towering black pointed toe heels. 

She got into the spirit of the sport by donning a crisp white baseball cap and styled her long blonde tresses in loose waves beneath. 

The Thank You Next hitmaker wore a funky pair of green tinted round glasses from Tiffany & Co. and a pair of chic gold-and-pearl hoop earrings from Mejuri while sipping on a drink.