At his lowest moments on the biggest of stages Daniil Medvedev could have been forgiven for regarding Rafael Nadal as his very own tennis version of the boogeyman.

The Russian has emerged as a major force in the men’s game over the past 18 months, but in that time the Spaniard has unwittingly been his tormentor-in-chief, punishing one of the NextGen youngsters for making moves to upset tennis aristocracy and giving the 24-year-old more than a few sleepless nights.

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This evening the red-hot world number four has an opportunity to vanquish his Rafa demons once and for all and take a huge step towards lifting what would be the biggest title of his career-to-date.

Daniil Medvedev

Image credit: Getty Images

Nadal sits within a tennis triumvirate that Medvedev and his peers grew up watching from afar. He has evolved from a famed sporting hero into a very real antagonist at the other end of the net, one who has soured the occasion on many of his significant firsts at the top of the sport.

It was Nadal who dismantled him in his maiden Masters 1000 final at the Canadian Open last year, dishing out a humbling bagel along the way.

The Mallorcan was waiting for him in his first Grand Slam final just weeks later too, cruelly edging Medvedev in a five-set thriller after he had hit back from two sets behind.

And it was Spain’s Raging Bull who inexplicably triumphed from 5-1 and then a match point down in the deciding set in last year’s ATP finals round-robin, thus denying the Russian a first win at the event on his debut week at the season’s finale.

That painful loss ensured an excellent year ended on a subdued note for Medvedev. It could even have contributed to a subconscious lull that stopped him continuing his relentless rise in the early part of 2020, before the pandemic brought everything to a halt.

By his own admission, that third loss to Nadal took some weeks to come to terms with but he is very much lighting up the tennis world once again now.

If 2019 was a breakthrough year, then this tournament and the semi-final showdown with Nadal in particular, could be a watershed moment.

Daniil Medvedev lines up a backhand

Image credit: Getty Images

The Russian has enjoyed another surge on hard courts in the latter part of the season, culminating in a third Masters 1000 title, this time in Paris-Bercy, and a perfect run in the round-robin at the O2 Arena.

His form is such that many were tipping him as the favourite to leave London with the biggest trophy of his career long before he made the last four.

There’s just the small matter of finally vanquishing that boogeyman first.

Nadal often represents the biggest physical challenge in tennis, but Medvedev’s short and painful history facing the 20-time Grand Slam champion means this could be more significant as a mental test that he must overcome.

For a man who loves chess, the psychology and strategy involved in trying to solve the Nadal puzzle will be one that has both excited and frustrated him in equal measure.

Eurosport expert, Mats Wilander has hailed Medvedev as a tactical genius and has even likened him to a chess player on a tennis court given his ability to adapt to the situation in front of him.

He will need to call upon that and then some given that Nadal is also regarded as one the sport’s great problem solvers.

So far he has outmanoeuvred Medvedev in their meetings, but the Russian could do worse than take heed of the words of his compatriot and chess grandmaster, Garry Kasparov in searching for that maiden victory.

“Winning is not a secret that belongs to a very few, winning is something that we can learn by studying ourselves, studying the environment and making ourselves ready for any challenge that is in front of us.”

Medvedev says he enjoys playing all of the 'big three' and has slowly learned lessons in his three matches with Nadal, improving from a convincing defeat to one where he was on the brink of victory.

He knows the moves and tactics that can do damage to Nadal, it’s just a case of taking that final step to provide a checkmate and put those old demons to bed.

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