These are our top 10 moments from Wimbledon’s long – and legendary – history

It’s the oldest (and arguably most prestigious) tennis tournament in the world. But what makes Wimbledon so completely iconic?

We’ll give you a hint: it’s not the strawberries and cream served on Centre Court that has us coming back year-after-year.

It’s the excitement of the game.

It’s the unquestionable skill of the players.

And it’s the way Wimbledon is a perfect microcosm of the best of British ideals: a mix of strict tradition, stricter sportsmanship, and of course, a fine appreciation for the ridiculous when it’s at work.

Be it an extraordinary match, or a spectacle unfolding in the stands, these are the 10 racquet-making moments that keep us glued to the screen and court.

How many do you remember?

1996: No strokes – just streaking

Let’s set the scene: it’s 1996 and the men’s Wimbledon finale is about to start.

We’re talking 14,000 odd spectators in the stands – including a packed royal box – waiting for the faceoff between Richard Krajicek and MaliVai Washington.

It’s a match that will define the former’s career.

The players warm up and pose for photos. The audience watches with a sense of calm anticipation.

And then…

The streaker appears.

Can you name a better way to steal the limelight than running across Centre Court in nothing but a caterer’s apron?

Was it a political protest? Publicity stunt?

Maybe, if that’s what you call the average 23-year-old craving a bit of very public exhibitionism.

Flashing the players, the world and the royal box – not our idea of a good time, personally.

But what a story to tell your grandkids. 

1996: Singing in the rain

Was there something in the water in 1996?

Wimbledon that year was basically unhinged.

As if a streaker in the final wasn’t enough, spectators were treated to a live, impromptu concert in the stands.

The rain came down, play was suspended and the crowd? They needed entertainment.

Cue: Sir Cliff Richard showing off his vocal chords.

And even enlisting previous tennis-pros like Virginia Wade, Martian Navratilova and Gigi Fernandez as your backup singers.

Imagine going to Wimbledon and getting a bonus 20 minutes of Sir Cliff belting out the tunes. The box office should’ve charged double that year.

And just like the streaker, the spectacle overshadowed the match. It made front-page news in all major British newspapers the next day.

Since Wimbledon installed a retractable roof in 2009, we’re not likely to see a repeat celeb performance. But forgive us if we daydream of a world where we might see Harry Styles singing at Centre Court.

2015: Williams vs Williams

We love a good old-fashioned rivalry, and sport has produced some of the best.

But a rivalry between sisters? We can’t imagine anything more intense.

Serena and Venus Williams have been ranked 1st and 2nd respectively, in both singles and doubles. Twice over.

Any match pitting them against each other is literally a case of legend against legend. But they hadn’t met in a grand-slam event for six years when they faced each other in 2015.

Imagine sitting in the stands that day.

Imagine facing your own sister across the court.

Serena was the ultimate victor, but it took until the seventh set of the game for her to take control of the match.

These sisters have too much respect for each other not to give it their all, and we love that.

So, if you asked us to pick a favourite? Sorry, no can do. It’s a tie.

2002: The wildcard takes the prize

Usually we love a dramatic exit, but Pete Sampras’ final departure from Wimbledon is a heartbreaker.

In 2002 he had seven Wimbledon titles under his belt, and had never lost a finals match. From 1997 he’d been on a Wimbledon winning streak, taking four straight titles home.

Not bad going, Sampras!

Safe to say, no one expected him to lose in 2002 - and especially not against a wildcard, on Court Two.

Because George Bastl didn’t even qualify for the tournament. He was ranked 145th in the world and only got into the main draw down to chance.

But he won the first two sets.

Sampras won the third and fourth, but fumbled the last set and ultimately, lost the match.

Stunned, he stayed seated in silence for a long, painful moment, before leaving court with his head down.

This picture of dejected defeat is all the more heart-wrenching in retrospect: Sampras never returned to play singles at Wimbledon again.

Wimbledon Centre Court

Wimbledon

1993: Jana Novotna weeps

It’s 1993 and Jana Novotna has just lost the Wimbledon finale against Steffi Graf.

It’s nothing new: any tennis match has a winner and a loser to show for it at the end. But something about this particular game had emotions running high.

Novotna had started with a sizeable lead on her opponent and then ‘choked’, letting the match – and her first shot at a grand-slam title – slip through her fingers.

Honestly, we’d have been watching it through our fingers.

Still, Novotna held it together – at least, until she was handed the runner-up trophy.

Getting so close to your dream and falling short must really sting, because it bought a cascade of tears to her eyes. And down her face.

She mopped up on the Duchess of Kent’s shoulder.

Did it break royal protocol? Totally. But it mended our hearts to see some honest compassion from royalty.

2022: The wrong call

This one should be seared into recent memory – it happened only three years ago.

And we’re giving it big points for drama, even if it’s the kind that leaves a bad taste in your mouth.

It’s the men’s singles final, and Nick Kyrigos has just accused a harmless spectator of being drunk and distracting him. He was so vehement about it that poor Anna Palus was unfairly removed from the stands.

She sued him after he accused her of having “700 drinks” at the match – and Kyrigos made a public apology, admitting he’d been mistaken and made a £20,000 donation to Great Ormond Street hospital to make amends.

It wasn't the first time Kyrigos’ behaviour has landed him in hot water either.

Earlier in the championship, he was fined US$10,000 for verbally abusing a line judge and spitting at a spectator.

Not unexpected, considering he’s had more fines for bad behaviour than any other player in history. 

Ranting? Trash-talk? Raquet-wrecking (say that five times fast)?

He’s done them all.

He may not be a paragon of good sportsmanship, but at least you know if you watch him play, you’re guaranteed some kind of show.

1981: The umpire’s fault

Kyrigos is not the first – or even worst – offender when it comes to unsportsmanlike conduct.

John McEnroe’s 1981 on-court rant is probably the most famous of all. But what happened?

It’s the first-round match at Wimbledon and an elderly umpire has dared to call a ball out.

The ensuing tirade from McEnroe has gone down in history; often being voted by fans as their favourite Wimbledon moment of all time.

It may even have inspired a scene if the 2004 film Wimbledon, when fictional wildcard player Peter Colt argues with the umpire for an out ball at a match point. There are definite similarities – “the chalk flew up” appeared in both the fictional and real-life rant.

And honestly, is there anything more iconic than calling someone “the absolute pits of the world” because you disagree with their judgement?

We’re saving that one.

Maybe we’ll unleash it next time the team bickers over punctuation preferences.

Tennis balls and racquets in shadow of the net

Tennis court

2013: Andy Murray finally comes out top

You probably remember this one.

After a 77-year losing streak, Britain finally got a male champion again.

2013 saw the well-deserved victory of Andy Murray – the first British man to win Wimbledon since Fred Perry in 1936.

Murray was one of the four most dominant players of professional tennis in the 2010s. But he wasn’t considered a favourite to win against Novak Djokovic in the 2013 finale.

He’d lost the year previously to Roger Federer, and struggled to hold his weight in matches against the big three (Federer, Nadal and Djokovic).

But 2013 marked a turning point.

Murray beat the Serbian player in straight sets, in a match lasting over three hours.

Three hours that were totally worth the sweat and tears, for a victory the UK could dine out on for weeks.

Or at least, until Murray’s second Wimbledon victory in 2016.

2019: A familiar face

Wimbledon is incredibly prestigious.

So, you don’t expect to see A-list audience members getting sloshed on too much Pimms, right in front of the cameras.

Woody Harrelson’s poison of choice might’ve been wine, but it had the same effect. He was caught by the keen-eyed among us, staggering around and being manhandled by security.

We bet organisers were wishing he’d never been allowed to return to his seat.

Once courtside, Harrelson pulled a series of bizarre expressions for the camera.

Sober? We couldn’t comment – but note that no irate player tried to boot him from the audience.

Safe to say, we don’t remember much about the match itself.

2008: Nadal finally gets his shot

We’ve saved the best – or certainly our favourite – for last.

If you grew up watching Wimbledon in the 2000s, you’ll know Roger Federer is basically the god of tennis.

Greatest player of all time? We’d say so.

Who else has won the men’s singles at Wimbledon a staggering eight times? Or been ranked #1 for a record-breaking 237 consecutive weeks?

But at Wimbledon in 2008, his long winning streak finally broke.

Pitted against Rafael Nadal in the final for the third consecutive year, expectations were running high. Federer had triumphed on the previous two occasions, but Nadal wasn’t an easy opponent to beat.

The match was full of drama.

Rain disrupted it twice.

Nadal and Federer both kept winning sets, one-upping each other through the match, making it impossible to predict a winner.

There was even an exciting fourth set tie break keeping everyone on their toes.

But when the moment came, Nadal finally beat Federer when the latter was just two points away from winning his sixth consecutive Wimbledon title.

It’s still considered the greatest professional tennis match ever played.

And it marked a turning point in Federer’s career, with his record-breaking stint as world no.1 going to Nadal that year.

But it didn’t keep him down for long. Before retiring from professional tennis, Federer would regain the top ranking on a further three occasions.

We’d give a lot to watch this legendary match for the first time, all over again

Start your summer with Wimbledon

You know summer has arrived when Wimbledon starts. But when the championship is over, it’s time to get out the house for a summertime drive.

So why not take a picnic to enjoy with some beautiful scenery?

Pack some British strawberries to sample, close your eyes and pretend you’ve just returned from watching the Wimbledon finale.

We call that a perfect British summer.

Chloe Allen

Chloe Allen

Our Digital Marketing Executive Chloe is in charge of our e-newsletter. There's no one better placed to inform and delight you every month, so keep your eyes peeled for her newsletter hitting an email inbox near you soon.