Now that’s what you call a dynamic duo at Wimbledon — British music sensation Cliff Richard and legendary actor Robert Redford. The two upped the glitz quotient in the women’s semi-final between Victoria Azarenka and Petra Kvitova at the 2011 Wimbledon Tennis Championships.
We don’t know whether they were friends or knew each other. But it’s quite possible they might have crossed paths at some point in the entertainment world which is reportedly very small. Still, seeing these two legends in the stands is quite the treat — like a timeless snapshot of a bygone era with the best music and films.
A Historic Royal Appearance
If there’s one event where you’re likely to spot a British royal, Wimbledon is definitely it – especially if a game involves Andy Murray. Prince William and Princess Kate attend often. Pippa Middleton is somewhat of a permanent fixture too. But this picture here is particularly special. It's not just another royal appearance. It marks the first tennis match since World War II broke out, also known as the “Victory” match.
As the war raged on for six years, over 1000 bombs fell on the town of Wimbledon. One even landed on the Wimbledon Center Court. Although most of the damage was repaired only by 1947, the spirit of Wimbledon lived on. Pictured here are Queen Mary, The Duchess of Kent, and Princess Nicholas of Greece. Seated alongside them were Group Captain Sir Louis Greig, Brig-General EF Koenig, and Air Chief Marshal Sir Arthur Tedder.
King George VI
What is the royal family’s connection to Wimbledon? Many royals attend for the love of the sport. Some attend just because. But it's much more than that. Attending Wimbledon is a royal tradition. In 1907, Prince George and Princess Mary attended Wimbledon for the first time, and something clearly stuck. Tennis had them enthralled and swept up, despite who they were.
When he became King George V in 1910, he became the patron of The All-England Lawn Tennis Club. Pictured here is his son, King George VI, and other members of the royal family watching Wimbledon. What’s more, King George VI even competed in the Men’s Doubles in 1926 with Sir Louis Greg. He was still the Duke of York then. Things didn’t go well. The pair lost three straight sets! Expectedly, they were gracious and dignified in defeat.
Tricia Nixon
Richard Nixon’s daughters, Tricia and Julie grew up in the public eye. Along with her sister, Tricia performed ceremonial duties and represented the United States wherever she went. In June 1969, she arrived in London to watch Wimbledon. Her father was in the country to represent the United States at the investiture of Prince Charles of Wales. Soon after, the press began hearing about matchmaking efforts.
Both Prince Charles and Tricia Nixon were single. The two represented the future of their respective countries — countries that were allies in every way. It seemed like a perfect match! Despite everyone's efforts (Prince Charles even visited Washington DC the following year), this match did not stick.
Princess Anne
Here’s a throwback to July 7, 1967, with the young Princess Anne watching the final showdown between John Newcombe and Wilhelm Bungert. Much like some other members of her family, Princess Anne isn't a Wimbledon enthusiast. She would much rather be around horses instead of in the Royal Box.
Plus, her heart belongs to rugby, and she's been the patron of the Scottish Rugby Union since 1986. It seems the Princess takes after her mother in her indifference to tennis. Despite the late Queen being the patron of the tournament, she only attended Wimbledon four times during her 70-year reign.
Doreen Dawne
This picture transports us back to the 1967 Wimbledon Tennis Championships and the lady in focus is the fashionable Miss Doreen Dawne. One can only imagine how her outfit, complete with a fabulous hat was all the fashion rage back then. She symbolizes an era where tennis wasn't just about skill and competition, but also about making a fashion statement.
Safe to say that not much has changed in that respect over the years. Wimbledon still gives us some of the most memorable fashion moments. The only difference? Celebrities aren’t always striking a pose but refreshingly relaxed – their faces a full spectrum of genuine emotions while still looking ultra chic.
Rod Taylor, Christopher Plummer, and Camilla Sparv
Now that’s what we call star spotting at Wimbledon. The entire gang seems to be here! On this day in 1967, actors Rod Taylor, Christopher Plummer, and Camilla Sparv were spotted in the stands at Wimbledon’s Center Court. Surrounding them were a whopping 175 extras.
The excitement and anticipation were palpable that morning, and it shows! This crew had gathered to recreate the exciting games that had unfolded just the previous June. The reenactment was part of a new film project that included scenes set at Wimbledon. The film, titled "Nobody Runs Forever," was a production by Betty Box and directed by Ralph Thomas.
Bing Crosby
From time to time, famous crooners not only make their way into our hearts, but to the hallowed grounds of Wimbledon as well. One such memorable moment was in 1965 when Bing Crosby was spotted in the crowd. Spectators were star-struck even more than usual on spotting the singer enjoying the games.
Crosby’s star had risen significantly in the 60s. His songs were regular fixtures everywhere you went. He was also an actor on the big and small screens — quite a multifaceted talent. It’s not surprising why photographers descended on the star when he arrived in London. Anything for a glimpse of Bing Crosby!
Princess Margaret
In 1965, Princess Margaret was spotted in the stands at Wimbledon looking ever so glamorous. She was seen wearing stylish sunglasses and a large hat. It wasn't uncommon to see her enjoying a cigarette during the matches, as was the relaxed custom at the time. Princess Margaret was especially popular during the 60s.
Her attendance was a highlight for any event during that decade. She elevated any gathering and made it fashionable and hip. It’s not an overstatement to say that she was one of the most popular members of the Royal Family during that time. The world loved her for her candor, a wit that could cut deep, and her easy-going ways.
Queen Elizabeth II
When Queen Elizabeth II attended Wimbledon, you knew the occasion was extra special. She rarely ever visited. The monarch was famous for many things, particularly her indifference to tennis. But in 1977, the Queen graced Wimbledon to watch the finals between Virginia Wade and Betty Stove.
It would be three decades later (a staggering 33 years to be precise) before the Queen returned to Wimbledon in 2014 to cheer on home boy Andy Murray, of course. It's not very often that she would watch a tennis game but Andy Murray is always a good reason. During her visit, she also met Serena Williams, Billie Jean King, and Martina Navratilova.
Judy Huxtable
In a stylish throwback to June 22, 1960, British actress and model Judy Huxtable was spotted at the Wimbledon Tennis Championships. Don’t miss her fabulous pillbox turban hat. Judy Huxtable was a famous society debutante of the time. She was one of the faces of the vibrant "swinging London" scene in the 60s.
As a model, she was represented by the William Morris Agency, and her face graced ads for Bacardi rum and Fry's Chocolate. Judy Huxtable's on-screen appearances included roles in films like "Les Bicyclettes de Belsize" (1968) and the cult classic "The Touchables" (1968). She would also venture into the world of horror films.
Prince Charles
Pictured here is a young Prince Charles at Wimbledon's Centre Court in 1970. He appears engrossed in a match between Dennis Ralston and John Newcombe. We say “appears” deliberately. Everyone knows that he isn’t a big fan of watching the sport but he seems to be taking quite an interest here.
King Charles may have inherited his lack of enthusiasm for tennis from his mother. Like her, he’s rarely ever seen at Wimbledon. However, he was spotted watching Roger Federer's game from the Royal Box in 2012. It marked his first visit to Wimbledon in a whopping 42 years!
Diana, Princess of Wales
When it came to owning Centre Court fashion, nobody did it like Diana, Princess of Wales. She was an avid tennis fan and a familiar face at tennis matches during the '80s and '90s. Here we see her in her style element – cheerful summer print, blue floral wrap dress, and a crisp white shirt. It’s easy breezy and delightful, much like her.
Lady Diana was famous for rocking oversized '80s belts, bold power shoulders, and retro shades in the stands. Her colorful outfits were almost as exuberant as her animated expressions during intense matches. Here she is watching the iconic John McEnroe VS Björn Borg game in the ‘80s.
Cliff Richard and Sue Barker
The story of how musician Cliff Richard and tennis player Sue Barker first met is rather intriguing. He first laid eyes on Barker when she was celebrating a tournament win in Brighton in 1981. He was accompanied by his Shadows bandmates at the time but mustered up the courage to ask her out on a date. He was 41 and she was 25. The pair’s romance was sweet but short-lived. They dated for less than a year.
Pictured here is the couple in happier times at Wimbledon. Barker later mentioned that they hadn't taken their relationship further due to busy schedules. After some time apart, Sir Cliff allegedly stopped contacting her altogether and the romance faded. They managed to stay friendly, although Barker has expressed frustration about Sir Cliff discussing their relationship ad nauseam in interviews.
John Lloyd and Deborah Taylor-Bellman
John Lloyd and Deborah Taylor-Bellman look engrossed while watching a match between Chris Evert and Martina Navratilova. Seated right in front of them is World Middleweight Boxing Champion Sugar Ray Leonard. The star power is alive and well in this shot!
Lloyd and Taylor-Bellman were a prominent “it couple” in the 70s and 80s. Lloyd was known for his skills on the tennis court, reaching several Grand Slam finals. Taylor-Bellman was a dance teacher and actor. The couple split after almost 30 years of marriage in 2016. They share two children together. Lloyd moved to Florida soon after the divorce.
Margaret Thatcher
Margaret Thatcher is known for her tireless work ethic, strong convictions, and her ability to evoke divided opinions even long after her passing. One thing she wasn't known for was a natural affinity for sports. According to her successor, John Major, she made occasional attempts to show interest.
Thatcher dutifully attended major sporting events, but it often seemed like an unfamiliar territory. This shot of her during the 1983 Wimbledon games seems to corroborate it! As Lord Coe put it, she didn't truly grasp the essence of sports until it extended beyond the sports pages or had an impact on other policy areas, which it often did during her time in office.
Robin Givens
Spotted at Wimbledon in 1994: actor Robin Givens watching a match between Lori McNeil and Kristie Boogert. The American actor was a rising star in the entertainment industry during the ‘90s. Her first acting stint was an appearance on “The Cosby Show.” She is best known for playing Darlene Merriman in the ABC sitcom "Head of the Class" in 1986.
Givens was a permanent fixture on the show throughout its five-year run. But her tumultuous marriage to boxer Mike Tyson would garner more attention than her contributions to the small screen. The marriage garnered significant media scrutiny, as did their eventual contentious divorce.
A Young Prince William With His Mother
Prince William was nine years old when he attended Wimbledon for the first time with his mother, Princess Diana, in 1991. Here we see mother and son seated in the Royal Box at Center Court. Princess Diana is at her stylish best — chic purple blazer and a belted white pleated skirt. The adorable duo seems happy and engrossed in the match.
Diana was often spotted at Wimbledon, much like her daughter-in-law Kate, is in the present day. Princess Kate not only loves playing tennis but is also the patron of the All England Lawn Tennis Club. She’s happily taken over the reins from Queen Elizabeth II who was a reluctant attendee at best.
David Hasselhoff
For anyone who needs a recap, David Hasselhoff was the face and soul of "Baywatch" despite what anyone tells you. It was no mean feat given the massive star power and eye candies on the legendary show. Hasselhoff’s charm catapulted him to global heartthrob fame during the 90s.
Pamela Bach, on the other hand, was an actress and producer, known for her work in film and television. The two of them together at Wimbledon in 1990 upped the glam quotient of the tournament. Hasselhoff and Bach married in 1989 before getting divorced in 2006. The former couple are parents to two daughters — Taylor Ann and Hayley Amber.
Eric Clapton and Tatum O’Neal
Eric Clapton and Tatum O'Neal attended the 1991 Wimbledon together. While they seem to be enjoying each other and the match, the events leading up to this moment were heartbreaking. Clapton was supposed to take a break that same year after extensive touring. In March of that year, his son, Conor, met a tragic, accidental death.
The unbearable loss had him withdraw from public life for a while. Clapton retreated to his summer home near London to grieve in private. The musician began slowly reemerging and reconnecting with the world that summer, as seen in this poignant moment with Tatum O’Neal.
Charlton Heston
There is no denying that Charlton Heston lived and breathed tennis with an incomparable passion. The man even hoped to become a Wimbledon club member, which amused his friends to no end! Need they remind him that the only way to do that was by winning the title?
Seemingly impossible dreams aside, Heston was not one to give up and achieved the next best thing. The actor went ahead and became a member of the prestigious All England Club. Very few actors in history have ever earned that privilege. He's pictured here looking absolutely in his element at one of the Wimbledon tournaments.
Billie Jean King
Few things make tennis fans happier than spotting Billie Jean King at Wimbledon. King’s influence extends far beyond tennis. She’s perhaps best known for winning the historic "Battle of the Sexes" match. King trounced her opponent Bobby Riggs in straight sets, and a new era for women in sports was born. King said afterward she felt tremendous pressure.
A defeat could set women in tennis back at least five decades. Beating a 55-year-old man gave her no thrills. Changing the possibilities for tennis was the ultimate validation. This 1994 picture shows King cheering on Martina Navratilova during her final match against Conchita Martinez. King continues to show the way. She advocates tirelessly for the rights of women and the queer community.
Tom Cruise and Nicole Kidman in Happier Times
Tom Cruise and Nicole Kidman were quintessential media darlings in the ‘90s. Cruise was almost synonymous with Hollywood glam and success back then. Kidman's star was steadily on the rise as a versatile, immensely talented actor. We see the former couple here in happier times at Wimbledon.
More than just a moment in time, it's a glimpse into the pop culture history of an era. It was hard to miss the mania surrounding this high-profile relationship unless one lived under a rock buried deep in the ground. Fans worldwide just couldn’t get enough and the press was forever in a tizzy around the couple.
Brooke Shields Cheering on Andre Agassi
Brooke Shields has been blissfully married to writer and producer Chris Henchy since 2001. But before Henchy, the world knew her as the better half of former world number one tennis player, Andre Agassi. This picture from 1995 captures Shields watching her then-boyfriend, Agassi, during the Wimbledon Tennis Championships in London.
Agassi won against David Wheaton, 6-2, 3-6, 6-4, 6-2. Shields and Agassi were together for six years and seemed like an endgame. Things didn't end well. Among the numerous reasons for their split were Agassi’s busy schedule and his alleged substance dependency problems. Fans the world over were heartbroken.
George H.W. Bush and His Wife, Barbara Bush
Say what you will about Bush Senior, but he led an extraordinary life. Besides his political legacy, he will also be remembered for his love of sports. Perhaps no other President has been such an enthusiastic and talented tennis player. Among his first tasks on becoming President was expanding the White House tennis court.
His love for the game isn't surprising. It began early thanks to his mother, Dorothy — a nationally-ranked tennis player. In this picture, he’s seen flipping through the pages of a booklet at Wimbledon with his wife, Barbara. He continued playing tennis until his hip replacement surgery in 2020.
Richard Dreyfuss
Look who’s repping Hollywood at Wimbledon – actor Richard Dreyfuss at a Sebastien Grosjean vs Tin Henman match. He looks like he has something to say about the game too. Remember Dreyfuss from films like “Jaws” and “Stand By Me?” He was a familiar face in Hollywood during the 70s and through the 90s.
Fast forward to today, and Dreyfuss has been making headlines of a different kind. The actor's views on new diversity and inclusion guidelines at the Academy Awards are well-known (try infamous and controversial). He's gone out on a limb, calling the proposed changes numerous things, including "patronizing" and "thoughtless."
Johnny Carson and Alexis Carson
It wasn’t uncommon to find Johnny and Alexis Carson enjoying a game at Wimbledon. The couple lived a lavish lifestyle, traveling the world and collecting multiple grand properties. They married in 1987 and enjoyed a loving 18-year marriage until Johnny Carson's passing in 2005.
The Tonight Show was never quite the same after his death. Johnny Carson was a heavy smoker. He succumbed to respiratory failure caused by emphysema, with his wife by his side till the end. Today, Alexis has a reported net worth of $300 million and she shares nearly half of it with her husband's foundation.
Matthew Perry
Photographers captured the late, great Matthew Perry’s day out at Wimbledon, and here's a surprising factoid about the man who became Chandler Bing. At age 15, Perry was among the top three tennis juniors in Canada. He might have been in Wimbledon – either on the court or in the commentary box – had life played out differently.
But his tennis dreams took a hit after a major tournament defeat in Los Angeles. That's when he realized that his overwhelming desire for fame needed to be fulfilled elsewhere. As he puts it, "I wanted it so much, I had steam coming out of my ears." Enter Hollywood!
Bridgette Wilson
In September 2000, tennis ace Pete Sampras and model Bridgette Wilson decided to tie the knot, surprisingly just nine months after they started dating. Pete Sampras, who was approaching the end of his illustrious tennis career, eventually hung up his racket a couple of years later after scoring a final Grand Slam win at the 2002 US Open.
Sampras once shared how he always dreamt about who he was going to marry and thought about where she was. He no longer had to dream it when he met Wilson. It’s evident that she’s his rock, steadfast often being there to watch his matches and cheer him on from the sidelines.
Sir Ian McKellen
This one’s a classic case of when two British national treasures meet — Sir Ian McKellen at Wimbledon. The actor is soaking up the tennis action, watching the ultimate face-off between Andre Agassi and Todd Martin with binoculars, no less! Fans love nothing more than spotting Gandalf the Grey in the stands.
While the on-court action is undoubtedly engaging, McKellan’s full spectrum of emotions is as entertaining to watch. From outrage and despair to unfiltered delight – pictures of his facial expressions could piece together a narrative of any game. Quite a treat for anyone who gets to enjoy them!
Tom Cruise and Mark McCormack
Tom Cruise and Mark McCormack were spotted together at Wimbledon in 2000 — two massive forces in their respective fields combined. McCormack was a trailblazer in sports marketing. It's safe to say he created the niche through sheer vision and grit. His incredible career kicked off alongside golf legend Arnold Palmer in 1960.
Together, they laid the groundwork for what would become the International Management Group (IMG), a driving force in sports marketing. In a touching tribute, the 2004 film "Wimbledon" pays homage to McCormack who passed away on May 16, 2003. His contribution to sports as we know it today endures.
Woody Harrelson
Woody Harrelson's been a Wimbledon regular for quite some time. What's cool about him is his unconventional style at these tournaments. However, on this particular occasion, he seems to have dialed it back a bit, which is quite unusual for the actor who usually shows up in fun fedoras or beach looks.
But what remains intact are his animated reactions during the matches. They've actually turned into some hilarious internet memes. We’ve even come across tweets where people say they don't watch tennis, they watch Woody Harrelson watching tennis. Watching the actor delight in tennis has become a kind of national pastime in itself. He's just one of a kind.
Tom Hanks and John McEnroe
Just when Tom Hanks thought he was there for some top-notch tennis action, who else popped up in the crowd but John McEnroe? Hanks looks suitably surprised and taken aback, probably a little awkward like the fans around him. What’s also intriguing is how these two icons from entirely different worlds shared an interesting connection.
The two were always wrangling with each other, not always the best of friends but still sharing a unique camaraderie. One can almost hear an incoming inside joke through this photo. It's moments like these that make Wimbledon not just about tennis but humanizes the sport and the celebrities we know and love.
Jack Nicholson
The one and only Jack Nicholson graced Wimbledon with his presence in 2001 to watch the Men's Final between Patrick Rafter and Goran Ivanisevic. Nicholson’s been quite the regular at Wimbledon over the years. He's not just a spectator but a full-blown cheerleader. John McEnroe once shared a memorable story about the actor.
The tennis ace was on the court, up against Jimmy Connors. Celebrities could sit right on the court's edge in those days. Jack Nicholson was only three feet away! McEnroe, who was a big fan, got pumped up by his presence. Nicholson kept shouting, "Johnny Mac! Johnny Mac!" The support fired him up and he won the match that day.
Bill Clinton Chats With Gary Richardson
Let’s go back in time to the 2001 Wimbledon Championships where the weather's acting up. As the rain pours down, fans are left twiddling their thumbs on Center Court. But showing up unexpectedly to save the day is none other than former President of the USA, Bill Clinton.
He decides to chat with BBC reporter Gary Richardson while they wait for the rain to give them a break. The second day of the Men's Semi Final match, featuring Tim Henman from Great Britain and Croatia's Goran Ivanisevic, was a complete washout. Clinton stepped in to add a bit of cheer to the gloomy day. Unexpected moments like these make Wimbledon unforgettable.
Paul McCartney and Heather Mills
Pictured here are Sir Paul McCartney and his then-wife, Heather in the stands in 2002, cheering on Lleyton Hewitt. Those were happier days for the couple. After her divorce from Sir Paul in 2008, Mills received a substantial settlement of £24.3 million, along with annual payments for a nanny and school costs for their child.
Although she once vowed never to walk down the aisle again, Mills surprised everyone in 2021. She had a private wedding with her businessman boyfriend, Mike Dickman, who was 36 at the time. Life, with all its twists and turns, can indeed be quite a journey.
Jude Law and Sienna Miller
Here’s rewinding to 2004, at the Wimbledon Lawn Tennis Championship. What made it extra special? Photographers spotted and snapped actors Jude Law and Sienna Miller in the stands, catching the quarter-final match between Tim Henman and Mario Ancic from Croatia. Law and Miller were the indisputable 'it couple' of the early Noughties.
They were even engaged at one point, but things got a bit rocky after Jude's highly publicized extramarital activities. They did give it another shot, but in the end, they decided to part ways for good in 2011. Like Wimbledon, Hollywood love stories can be an insane rollercoaster.
Linda Barker and Gordon Ramsay
It’s July 2004 at Wimbledon, and it's not just about tennis. It’s about the stars in the stands. The ever-charming Linda Barker and celebrity chef extraordinaire, Gordon Ramsay, were seated front and center, at the men's singles final match between Andy Roddick and Roger Federer.
Barker and Ramsay together were quite the visual treat – two legends of British television in one frame. The entertainment both on and off the court must’ve been off the charts on this day. One can imagine the pair itching to give expert advice true to their on-screen persona. But it looks like they refrained on this occasion.
Sir Sean Connery
Sean Connery is sorely missed by movie and tennis fans alike. This picture was taken in 2005 where he isn’t just waving to the gallery, but basking in tennis joy. Connery wasn't just a casual observer of tennis. He lived and loved it intensely.
The actor continued making appearances at Wimbledon and the US Open even after retiring from films. In fact, his final public outing was at the 2017 US Open to watch a match between Roger Federer and Frances Tiafoe. Over the years, Connery was often seen supporting his fellow Scot, Sir Andy Murray. The two remained close friends until Connery’s passing in 2020.
Pierce Brosnan and Keely Shaye Smith
Actor Pierce Brosnan and his wife, Keely Shaye Smith graced the royal box in 2007 during the Men's Singles quarter-final match between Rafael Nadal and Tomas Berdych. Their enduring love has defied the Hollywood marriage stereotypes. In an industry where relationships often make headlines for all the wrong reasons, Brosnan and Smith have shown that true love can withstand the test of time.
Brosnan has stood up for his wife when she was trolled online for weight gain. The couple is living proof that love, when genuine, can continue to grow and flourish, even in the most dazzling, often harsh and blinding of spotlights.
Sting and Trudi Styler
Music legend, Sting and his wife Trudi Styler were soaking in the fun on Center Court during the 2008 Wimbledon Championships. Their story is more than just a day at Wimbledon, it’s one of enduring love. Sting and Trudi didn't rush into marriage. They dated for a solid decade before saying "I do" in Wiltshire in August 1992.
Together, they've raised a beautiful family, welcoming four children into their lives: Mickey, Jake, Eliot, and Giacomo. It goes to show that some bonds only get stronger with time. Sting also has two other children from his previous marriage with Frances Tomelty.
Gwen Stefani and Gavin Rossdale
In this frame are musicians Gwen Stefani and Gavin Rossdale at the 2008 Wimbledon Championships. The couple is the postcard for wedded bliss here before things would fall apart. Stefani and Rossdale were married for nearly 13 years and shared three lovely children until rumors began to swirl that Rossdale had been a little too close with their nanny.
The "Voice" judge decided to file for divorce in 2015, and it was all finalized the following year. She said she fell apart during this time. Not long after, Stefani started dating Blake Shelton who was also dealing with his broken marriage to ex-wife Miranda Lambert.
Justin Timberlake
It's 2009 and Justin Timberlake is deep in the Wimbledon action unfolding below. His connection to the sport goes beyond being a spectator. Timberlake's been known to show off his skills on the court every now and then. He's been spotted numerous times, getting out there to enjoy a game or two.
Timberlake has made multiple appearances at Grand Slam events over the years with a range of emotions as famous as he is! He’s entertaining enough as is. Put him in the Wimbledon stands and it’s better viewing than your regularly scheduled programming. Some news reports have even labeled him "the happiest fan in the world."
Ewan McGregor
Spotted at Wimbledon in 2009, it's Ewan McGregor catching some tennis. He was in the stands to watch Andy Murray give his all against Stanislas Wawrinka. What makes this story even more interesting is that Andy Murray thinks Ewan McGregor would be perfect to play him in a movie!
The tennis star is a big fan. Despite a 16-year age gap between them, Murray believes McGregor has the acting chops to pull it off. The two also share a Scottish connection, lest anyone forgets. Is Hollywood listening already? We’d give anything for this film to see the light of day.
Ben Stiller
Wimbledon 2010 saw Ben Stiller and wife, Christine, taking in some tennis action in the UK. Stiller is quite the tennis enthusiast, although he doesn't consider himself much of a player. He’s no tennis ace, not at all by his own admission. The actor once spoke about the time he crossed paths with Rafael Nadal which turned into an unforgettable – yet slightly mortifying – experience.
During an appearance on "The Tonight Show with Jimmy Fallon," Stiller recounted how he got roped into a match with Nadal. He confessed that he practically "died inside" during the encounter. It was like living a dream and a nightmare all at once.
Woody Allen, Ralph Lauren, and Russel Crowe
It's not every day you see a trio like this together — director Woody Allen, fashion maestro Ralph Lauren, and the Gladiator himself, Russell Crowe. The three were locked into an exciting men's singles final match between Roger Federer and Andy Roddick in 2009.
Woody Allen, the man behind numerous iconic films, always brings a unique touch to events. Ralph Lauren was probably keeping a keen eye on the style both on and off the court. As for Russell Crowe, he’s the tough but lovable guy everyone adores. The star power is intense in this frame. We wouldn’t have it any other way.
Diana Ross
Diana Ross sure knows how to add some star power to the game! The singer is keeping a close eye on what’s happening at Center Court during the 2011 Wimbledon Tennis Championships. Diana's not a stranger to the tennis scene. She's a frequent guest, and her stylish presence is always a hit.
Ross has even rocked the stage with the Harlem Gospel Choir before the groundbreaking women's singles final at the 2001 US Tennis Open. This was a special moment because it marked the first time that two African American women, Serena and Venus Williams, competed for the US Open title.
Cliff Richard and Robert Redford
Now that’s what you call a dynamic duo at Wimbledon — British music sensation Cliff Richard and legendary actor Robert Redford. The two upped the glitz quotient in the women's semi-final between Victoria Azarenka and Petra Kvitova at the 2011 Wimbledon Tennis Championships.
We don’t know whether they were friends or knew each other. But it's quite possible they might have crossed paths at some point in the entertainment world which is reportedly very small. Still, seeing these two legends in the stands is quite the treat — like a timeless snapshot of a bygone era with the best music and films.
Kate and William
Prince William and Princess Kate Middleton had a grand time together at Wimbledon in 2011. Kate went solo to Wimbledon in 2007 when she and Prince William were still dating. A few months after their wedding, she and her husband went together for the first time. They're always a cheerful pair in The Box, sharing cute moments such as this one.
They were also perfectly coordinated in white and blue. The couple has made numerous appearances together since then. Plus, they get really animated during the games which is unusual and refreshing for royals. It’s hard not to be swept up by Wimbledon, even if you’re royalty.
Anna Wintour and Shelby Bryan
Fashion icon Anna Wintour, and her partner Shelby Bryan, were spotted at Wimbledon's Center Court in 2015. watching the intense showdown between Novak Djokovic and Roger Federer. Wintour and Bryan first met at the 1997 New York Ballet's Benefit Ball. Both of them were married to other people then. Rumors of them dating began to circulate.
Expectedly, the tabloids went crazy and covered the story intensely at the time. Wintour was married to psychiatrist David Shaffer (they have two children together, Charles Shaffer and Bee Shaffer Carrozzini), while Shelby Bryan was in his second marriage with Katherine Bryan. Although the couple was together for many years, they quietly separated without the need for a big announcement.
Michael Sheen and Rachel McAdams
Michael Sheen and Rachel McAdams attended the 2012 Wimbledon Final together, looking very much in love. The lovebirds first met on the set of "Midnight in Paris" and insisted nothing happened until after the movie wrapped. Still, the press continually snapped convincing photos showing them looking quite cozy.
Thankfully, the pair didn't have to worry about keeping things hush-hush by the time Wimbledon came around. They seemed quite carefree and happy seated next to each other. By February 2013, McAdams and Sheen would be broken up. They allegedly had different ideas about their future as a couple and couldn’t meet halfway.
Gerard Butler and Bradley Cooper
In 2013, Andy Murray made history as the first British man to clinch the Wimbledon Singles title in 77 years. It was a thrilling day for tennis enthusiasts the world over, no doubt. However, it was equally exciting for those with a soft spot for dapper male movie stars donning pale suits and indulging in some good old public displays of affection right there in the Royal Box.
Just take a look at the sheer joy radiating from Bradley Cooper and Gerard Butler. Priceless bonding right there. And they sealed the unforgettable day with a selfie. Now, that's a day to cherish!
Kylie Minogue
Kylie Minogue was spotted in the Royal Box on Center Court during the eleventh day of the 2012 Wimbledon Championships. The Australian singer seemed to be going for a more understated appearance. Perhaps she wanted to blend in with the crowd, impossible as that may seem. She was quite focused on the tennis action and appeared to be enjoying it.
No public displays of affection this time with her boyfriend, Andres Velencoso. The couple's passionate kiss had caused quite a frenzy at the O2 in 2010 during the final of the ATP Masters. Spectators at Wimbledon expecting similar entertainment were in for a disappointment.
Ricky Gervais
Famous funnyman Ricky Gervais joined Andy Murray's coach, Amelie Mauresmo, to cheer on Murray. The British ace was facing off in the third-round match against Roberto Bautista Agut. Gervais seemed absolutely thrilled to be there! Andy Murray did not disappoint, dominating Agut in straight sets.
And with Ricky Gervais looking on from Murray's player box, it added some extra star power to the event! That’s quite a classic moment of British pride and camaraderie – two legends happy to be in each other’s corner. Murray and Gervais even had the time to chat after the game. They had never met in person before.
Keira Knightley and James Righton
Keira Knightley and her husband, James Righton sat in the Royal Box at Wimbledon, all set to enjoy the Ladies' Singles Final on day thirteen of the 2014 tournament. Knightley's excitement and smile are infectious. The actor and her musician husband have been together since 2011.
They were introduced by a mutual friend at a dinner party. Things moved pretty swiftly, and by May 2012, the pair decided to tie the knot. They opted for an intimate wedding ceremony in France. Now they're a family of four, with two lovely daughters whom they prefer to keep away from the public eye.
Hugh Jackman
In this frame is actor Hugh Jackman in the stands at Wimbledon in 2014. We know Jackman loves tennis. He probably loves Novak Djokovic a bit more, however. The actor proclaims his admiration for the champion every chance he gets. He might as well shout it out from a rooftop too.
The two have even engaged in fun online banter in the past, one even involving a challenge to a tennis match put forth by Jackman as a joke. The Serb invited him over to his home in Monaco. Djokovic even asked if Wolverine's claws would come out to play. Now that's a match worth watching.
Jim Parsons
Actor Jim Parsons was spotted at Wimbledon in 2014. Parsons sat in the players' box, cheering on his friend and Canadian tennis sensation Eugenie Bouchard. She was playing against Alize Cornet that day. What makes this day even more interesting is that the two finally met in person after a year of communication through their agents.
They both looked absolutely thrilled to make each other's acquaintance earlier on at the tournament. She called Parsons her "most positive supporter." He was a fan and wrote encouraging emails to Bouchard after every game. Bouchard loved Sheldon Cooper (because who doesn't?) so this was a friendship destined to happen.
Heidi Klum
Pictured here is supermodel Heidi Klum watching Roger Federer take on Milos Raonic in the Men's Singles Semi Final match in 2016. The German-American model doesn’t just enjoy watching tennis, she frequently hits the courts as well. Her super active and dedicated approach to life is probably the secret to her defying age.
The model has more energy than most 30-year-olds. Tennis, yoga, pilates, circuit training, trampolining, and more are routine for Klum. Despite being over 50 (you read that right) she looks fantastic. The former Victoria’s Secret Angel is the very embodiment of an active and healthy lifestyle.
Stanley Tucci
The actor known for his role in "The Hunger Games" couldn't contain his emotions while watching the 2017 Men's Singles Final between Jo-Wilfried Tsonga and Andy Murray. Is that boredom or excitement, however? Stanley Tucci is a regular Wimbledon attendee. The actor always dresses to impress at these gigs.
The man never ever disappoints his fans or serious fashionistas. His stylish outfits have consistently earned him a spot on the list of best-dressed at Wimbledon. From stylish suits to outrageous socks, the dapper Tucci is always memorable at any event. He certainly left a lasting impression with this one, that's for sure.
Beyonce and Jay-Z
Serena Williams had a little help from her friends at the 2016 Wimbledon Finals. Jay-Z and Beyonce were her special guests that day. Queen B was the ultimate cheerleader, even though some of the game's rules eluded her. Beyoncé and Jay-Z's presence turned up the star power a hundred notches for this game.
Williams defeated Angelique Kerber that day. She smashed and stormed her way to victory as she always does, and would win the 22nd Grand Slam title. With friends like these, world domination doesn't seem an impossible endeavor. Everything is possible with talent and incredible friends in your corner.
Priyanka Chopra and Nick Jonas
Priyanka Chopra and Nick Jonas graced the Wimbledon Tennis Championships in June 2023. Fans will remember day 13 of the tournament as the one when Marketa Vondrousova clinched a hard-fought victory against Ons Jabeur. Vondrousouva made history as the first unseeded women's player to win the championships.
It was a momentous day at Wimbledon for sure. As for the Jonases, they made quite the impression in the Royal Box and looked fantastic while doing it. Chopra wore an abstract print midi dress, while Nick rocked a brown tweed suit. The couple are big fans of the sport and shared cute, cuddly moments from the stands on Instagram later.
David and Victoria Beckham
David and Victoria Beckham were spotted in the Royal Box on day 13 of the 2012 Wimbledon Championships. The Beckhams have made Wimbledon a regular part of their summer calendar, often attending matches as a couple or with their children. Their son, Romeo, once had quite a penchant for tennis.
The couple even had an artificial grass tennis court built on their estate grounds for him. But it seems that Romeo's tennis mania has cooled off, prompting his father to make some big renovations at home. The tennis court no longer exists. In its place is a massive football pitch instead. The Beckhams probably realized that attending Wimbledon might be better whenever the tennis fever strikes.
Katy Perry and Orlando Bloom
Orlando Bloom and Katy Perry had a sweet Wimbledon date on day three of the prestigious tennis tournament in 2023. The couple, who originally crossed paths at a Golden Globes afterparty in 2016, couldn't help but get cozy while watching the matches. Perry was the picture of chic sophistication in a black top paired with an oversized polka-dot necktie.
Her new baby bangs and sunglasses channeled vintage Audrey Hepburn elegance. Bloom, looked dashing in a navy suit with stripes, which matched perfectly with his tie. The dark blue sunglasses gave him just the right touch of sophisticated mob boss flair.
Hannah Waddingham, Jameela Jamil, Sam Ryder, Ryan Thomas, and Lucy Mecklenburgh
The London tennis tournament is practically a celebrity hotspot, with more stars attending than at a trendy new restaurant. Check out this fantastic photo with celebs seated all in a row – next to, above, and below in all the upper and lower rows! We've got Sam Ryder on the top left, Hannah Waddingham in the top center and Jameela Jamil in the middle row.
On the bottom right are dynamic Ryan Thomas and Lucy Mecklenburgh. They might not have much in common otherwise apart from their A-list status. But there’s nothing like the exciting matches at the 2023 Wimbledon Championships to bring this lot together.
Tessa Thompson and Sabrina Dhowre Elba
Tessa Thompson and Sabrina Dhowre Elba took in all the Wimbledon excitement in July 2023. Thompson is best known for playing Valkyrie in the Marvel Cinematic Universe, where she's been part of two "Thor" movies and "Avengers: Endgame." Sabrina Dhowre Elba was Miss Vancouver back in 2014.
You might also remember her from shows like "Three Thousand Years of Longing" and "Dantai.” But most people definitely know her as the better half of Idris Elba. The couple is a force to be reckoned with. The Center Court’s appeal definitely went up several notches with these fabulous ladies in attendance enjoying some thrilling tennis.
Emma Watson
Emma Watson made a rare public appearance at Wimbledon 2023. The British actress, who has taken a step back from the limelight in recent years, chose to attend the final matches between Novak Djokovic and Carlos Alcaraz. To make the day even more special, she had her brother, Alex, by her side.
The actor was also seen at the event alongside her father for the women’s finals – a match she wouldn’t have missed for the world. It was an exciting moment for tennis as Marketa Vondrousova made history by becoming the first unseeded women's player to clinch the championship, narrowly defeating Ons Jabeur.
Judd Apatow and Leslie Mann
Judd Apatow and Leslie Mann enjoyed the opening day of Wimbledon 2023. Their daughter, Iris, was also there, even though she isn’t pictured here. The couple looked quite coordinated in matching sky-blue ensembles. Leslie Mann rocked a stunning blue and white floral Prada dress from the spring/summer 2022 collection, perfectly complementing Judd Apatow's light blue checked jacket.
Meanwhile, Iris completed the trio's appearance with a charming black and white polka dot drop waist dress from Miu Miu. The only one missing was Maude, their other daughter, to complete this family outing. There's always next year for that perfect family photo.
Lily James and Poppy Delevingne
Lily James and Poppy Delevingne brought serious star power to the Wimbledon 2023 men's final. The duo looked like they stepped off the pages of a fashion magazine. While they made heads turn with their elegant outfits, their tennis enthusiasm was less clear. They might’ve just been there for the glitz and glam.
But few people can resist the emotion that is Wimbledon. Either way, they seem to be enjoying themselves thoroughly. You might remember James from "Mamma Mia! Here We Go Again," and "Darkest Hour." Delevingne is a popular British model and socialite. The two made quite the impression at Wimbledon.
Eddie Redmayne and Hannah Bagshawe
Eddie Redmayne and Hannah Bagshawe have been together for ages. Their love story defies industry tropes. It is heartwarming to see them at events together year after year. Redmayne is best known for appearing in "The Theory of Everything" and the "Fantastic Beasts" series. Bagshawe is a public relations executive. She's been his rock throughout.
The couple made a joint appearance at the 2018 Wimbledon Men's Singles Final. They appear to be waiting for events to unfold while almost blending into the background and each other, like this is where they belong. Here's to more everlasting celeb romances at Wimbledon.
Jonathan Bailey, Ariana Grande, Andrew Garfield, Zawe Ashton, and Tom Hiddleston
Celebrity spotting at Wimbledon is common. It's mundane, even. But not when a group hang looks like this — Ariana Grande, Andrew Garfield, Tom Hiddleston, Jonathan Bailey, and Zawe Ashton chilling together at Wimbledon 2023. This bunch was there to watch the showdown between Novak Djokovic and Carlos Alcaraz for the trophy.
Grande rocked her new blonde hair, a transformation she made for her role as Glinda in the "Wicked" film. Garfield and Bailey looked like twins in their camel-colored outfits. Meanwhile, Tom Hiddleston, sitting one row ahead, wore a blue blazer and a matching necktie. Ashton, seated next to him, looked lovely in a navy dress with light blue flowers.
Drake
Drake's unexpected appearance at Wimbledon in 2018 created a buzz more than usual. What was different this time? The player on the court that day was his ex. Fans went back and forth — watching Williams on the court, watching Drake watch Serena Williams. And the background to this story is the infamous "Drake curse."
Throwback to 2015 when Drake was jokingly blamed for distracting Williams, resulting in her losing the 2015 US Open semi-final. Would history repeat itself? It sure seemed that way at the start. But she bounced back, winning the second and third sets. The curse had been lifted. Imaginary hexes aside, it meant beyond a doubt that Serena Williams was just that good.
Phoebe Dynevor and Pete Davidson
Phoebe Dynevor and Pete Davidson were spotted enjoying a tennis match on the sixth day of Wimbledon 2021. The outing marked their official debut as a couple — no place better than Wimbledon to make a relationship public. The couple couldn't hide their affection for each other.
The love being served up in the stands almost rivaled the courts that day. Davidson and Dynevor were caught on camera sharing sweet forehead kisses and side hugs. The "Saturday Night Live" star is known for his numerous high-profile relationships, women who rapidly turn into exes. Like other relationships before and to come, this one also bit the dust.
Benedict Cumberbatch and Tom Hiddleston
The 2019 Men's Singles final between Roger Federer and Novak Djokovic was intense, lasting four hours and 57 minutes. Djokovic claimed his 16th Grand Slam title after a nail-biter match. But the crowd’s attention was also drawn to the stands, where Benedict Cumberbatch and Tom Hiddleston presented themselves impeccably.
They personified the type of classic gentlemen you'd expect to see at an exclusive event like Wimbledon – polite, well-dressed, and the epitome of traditional tailoring. The actors wore their own classic shades of blue. Safe to say that Loki and Sherlock together were the other winners at Wimbledon that day.
Brad Pitt
Brad Pitt enjoyed the Gentlemen's Singles final at Wimbledon 2023. Seated next to Guy Ritchie, the actor rocked a blue knit polo and snazzy aviator sunglasses. It was the actor's first time at Wimbledon, but he's been a long-time fan of the sport.
It’s never too late to make an appearance at Wimbledon, and the wait was worth it for Pitt. 2023 was historic at Wimbledon in every respect. The tournament attracted the crème of the A-list crowd — David Beckham, Katy Perry, and Elle Fanning among them. The excitement on and off the grass court matches was through the roof.
Daniel Craig and Rachel Weisz
Daniel Craig and his wife Rachel Weisz were spotted at Wimbledon 2023 in a rare public appearance together. The couple joined Prince William, Princess Kate, and their children Prince George and Princess Charlotte in the royal box to watch the thrilling men’s singles final. The James Bond actor has a long connection with the royals.
The story goes way back to when Craig filmed a James Bond skit with the late Queen Elizabeth II during the 2012 Olympics. Directed by Danny Boyle, the scene garnered a lot of attention. Even the Royal family members were in the dark about it. That’s how big the secret was.
Jon Bon Jovi
Jon Bon Jovi was in the thick of all the Wimbledon action in July 2023. His animated facial expressions spoke volumes about how much fun he had. Not one to back quietly, Jon whistled enthusiastically to cheer on the players. He was seen chatting with other spectators. The rock legend’s love for the game has an unexpected connection to tennis player Cameron Norrie.
Their friendship developed after Bon Jovi watched Norrie play in Miami. Norrie shared how the two connected over a game and how the singer was “really liking tennis more and more.” Norrie was confident Jon would make an appearance at Wimbledon. He was right as it turns out.
Prince George and Princess Charlotte
Prince George and Princess Charlotte might be young royals, but the two lit up like any child would at watching the 2023 Wimbledon men’s final. George appeared to be guiding Charlotte through royal traditions and showing her the ropes like a good big brother should.
Kate and William decided to bring their two eldest children to the prestigious tournament for the final day. It was a return visit for 9-year-old George and a Wimbledon debut for eight-year-old Charlotte. Their mother later mentioned that Prince Louis, five, was a bit sad he couldn't join the fun! All in good time, young prince.
Shakira
Shakira rocked at Wimbledon in a funky denim one-piece. The look is very much in line with her distinctive style but traditional Wimbledon enthusiasts were up in arms. To be clear, she wasn’t flouting any dress code rules. Wimbledon enforces strict clothing rules for tennis players, which have faced controversy due to their inflexibility.
These rules can leave some athletes feeling limited in their self-expression on the court. However, there aren't any specific dress codes for the spectators. How about everyone sit down and just enjoy the game? Maybe count their lucky stars to be breathing the same air as Shakira.
Thomas Brodie-Sangster and Talulah Riley
Thomas Brodie-Sangster and Talulah Riley shared a kiss while enjoying a match at Wimbledon 2022. The couple’s love story began as co-stars on the set of FX's "Pistol." Soon enough, their on-screen connection turned into something more. The first hints of their romance were in 2021 when they were spotted holding hands in London.
After making their red carpet debut at the British Academy Film Awards in 2022, the two have had numerous PDA-filled outings together since such as this tender moment in the Champagne Suite at Wimbledon. Big news came in July 2023 when they announced their engagement.
Rami Malek and Lucy Boynton
Rami Malek and Lucy Boynton were all smiles and suitably animated during the 2022 Wimbledon Tennis Championships. They were among the best-dressed couples that year – Boynton in a white retro-inspired dress and Malek in a black suit and a contrasting striped shirt. They also looked completely smitten.
The couple had been together for more than four years by then, although they mostly kept a low profile. An unforgettable moment that brought them into the spotlight was when Malek openly expressed his love for Boynton during his 2019 Oscars acceptance. He won Best Actor for his fantastic performance in “Bohemian Rhapsody.”
Sabrina Dhowre Elba and Idris Elba
Sabrina Dhowre Elba and Idris Elba enjoyed a date at the Wimbledon 2023 men's final. It was difficult to tell which was the main event – the tennis match or the couple’s day out. Tennis almost faded into the background at some point. The couple first met at a party in 2017.
Just two years later, they sealed the deal with a lavish Moroccan wedding ceremony. Idris, who had previously declared he wouldn't marry again after his second marriage, seemingly had a big change of heart. He publicly proposed to Sabrina during a film screening before they exchanged vows in 2019.
Kate and Meghan
Catherine, the Duchess of Cambridge, and Meghan, the Duchess of Sussex, made history in 2018 when they stepped out for their first outing together without their husbands. The royals attended Wimbledon to catch the women's finals — a day royal enthusiasts are likely to remember for a while. All eyes were on them as they watched Serena Williams on the court.
Kate went for a timeless look while Meghan opted for something more casual and risqué by Wimbledon (and British royals) standards. Let’s just say that the event was intensely scrutinized by royal watchers, critics, media, and fashion police the world over.