Heather Watson v Serena Williams (2015)


It’s never nice to dub a player’s failure to win as a 'choke', but that, unfortunately, is what this was.

Before the match, Watson – ranked 59th at the time – had no reasonable expectation of defeating the greatest women’s player of all time.

The Brit’s chances were reduced even further after Williams took the first set 6-2.

Then, at 3-3 in the second set, Watson produced a standard of tennis she had never reached before (or since), winning six straight games to not only level the contest, but go a double break up in the decider.

She served for the match at 5-4, but the significance of what she was about to do – plus Williams’ resilience – got the better of her.

Williams duly broke, held her own serve and then broke again to win the match. Just over a week later, she won the tournament to clinch the second ‘Serena Slam’ of her career.

Watson’s career, meanwhile, has still not kicked on to the next level. It is not unreasonable to suggest that it might have done had she held her nerve against Williams. 

Tim Henman v Pete Sampras (1998)


No British player did glorious failure better than ‘Tiger’ Tim.

Before Andy Murray came along, it was Henman who carried British tennis’ hopes of a first male Wimbledon champion since Fred Perry.

His gutsy semi-final defeat to Sampras in 1998, where he played some inspired tennis before ultimately losing in four sets, only strengthened the belief of both the country and Henman himself that he would one day make history.

"That experience will be invaluable," said the Englishman afterwards. "I've seven or eight more years of playing this tournament if I stay injury-free.

"I think I've a good chance in each of those years and I'll continue to give it 100 per cent."

Sampras was even more emphatic in his assessment.

"I don't see any holes in his game," said the American, who went on to claim the fifth of his seven titles at SW19. "He'll break through and win this one year."

If only.

Henman reached three more Wimbledon semi-finals over the course of his career, losing each one in increasingly exasperating circumstances to that year’s eventual winner – Sampras (again), Lleyton Hewitt and Goran Ivanisevic.

Still, at least he has Henman Hill. Whatever happens in the future, that will never be taken away from him. 

Andy Murray v Roger Federer (2012)


"Right, I’m going to try this, and it’s not going to be easy…"

The hardest defeat – and post-match interview – of Murray’s career actually proved to be the making of him.

For a set and half, before the rain came and forced the Centre Court roof to be closed – a move which benefitted Federer – Murray was the better player. For the first time in four grand slam finals, he was not overwhelmed by the occasion.

And while Federer dominated the second half of the match, Murray – under the guidance of Ivan Lendl – came away from it knowing (finally) that he could match the greatest players over five sets.

His response to his most crushing defeat, of course, was phenomenal: he won Olympic gold at the All England Club – beating Federer in the final – four weeks later, and claimed the first slam of his career at the US Open later that year.

The following summer, he capped the greatest 12 months of his career by triumphing at Wimbledon.

It shouldn’t have needed it, but Murray’s tears during his dignified runners-up speech also caused a remarkable transformation in how he was perceived by middle Englanders. Overnight, he became a national treasure. 

Marcus Willis v Roger Federer (2016)


Willis was swatted aside by the Swiss master, but that didn’t matter.

For the then-part-time tennis coach, reaching the second round of Wimbledon and facing the greatest men’s player of all time on Centre Court was a remarkable achievement.

You only had to look at Willis – who sported a beer belly and Federer-style Nike headband – to know that he was not someone who took tennis or himself too seriously.

But in the lead up to the 2016 Championships, the Englishman – inspired by a new girlfriend – navigated six rounds of qualifying and the first round proper to earn his shot at Federer.

A first-set bagel aside, the then-world No. 772 held his own, managing three and four games in the second and third sets.

In what was an entertaining game, Willis even produced the shot of the match and tournament: a deft lob that left Federer stranded.

Irrespective of what Willis does or does not go on to achieve in tennis, that shot – and match – will live with him forever. 

Barry Cowan v Pete Sampras (2001)


Before Willis, there was Cowan.

He got significantly closer to victory over a seven-time Wimbledon champion, too, taking Sampras to five sets – a remarkable feat, given he lost the opening two.

So how was Cowan, who was ranked 248th in the world, able to match the then-king of the grass? By listening to music.

At each change of ends, the Liverpool supporter would put in his headphones and play You’ll Never Walk Alone on repeat, a tactic he decided on after speaking to a psychologist pre-match about how to handle the occasion.

Ultimately, Cowan was unable to cause what would have been one of the greatest shocks in sporting history.

He has, however, enjoyed a successful and lucrative career ever since, mainly working as Sky Sports’ in-house tennis 'expert'.

Not bad for a player whose playing career – that Sampras match aside – was less than unremarkable. 

Insider knowledge:

Which brand sponsors Andy Murray?

Andy Murray is sponsored by Under Armour, having signed a clothing deal with the American brand in 2015. Murray’s previous sponsor was adidas and, before that, Fred Perry.