Andrey Rublev will face a monumental challenge on Wednesday when he takes to the court to do battle with Daniil Medvedev in the Arthur Ashe Stadium. The No. 8 in the Pepperstone ATP Rankings has never progressed past the quarter-finals at a Grand Slam, despite having reached the round eight times in his career prior to Wednesday.

“Of course, he hasn’t got past it, but it’s much worse to lose in the last 16 and not have that opportunity again,” Fernando Vicente, Rublev’s coach, told ATPTour.com. “We see it as a positive, not a negative. We see it as another opportunity to try and do it. If it doesn’t happen, we will have to keep trying and keep working.”

He has set foot in the quarters in all of the Grand Slams: at the Australian Open (2021, 2023), Roland Garros (2020, 2022), Wimbledon (2023) and the US Open (2017, 2020, 2022, 2023).

In those matches, in search of a debut major semi-final, Rublev has faced Medvedev three times (including this Wednesday), Novak Djokovic twice and Rafael Nadal once, as well as Stefanos Tsitsipas, Frances Tiafoe and Marin Cilic. However, he has never been able to celebrate and progress to the semi-finals.

“The vast majority of times, six at least, he wasn’t ready, physically or mentally,” said Vicente. “The Cilic one at Roland Garros was a clear opportunity and he should have won, but he lost it in five sets and wasn’t able to manage the mental side of it. Now he is ready, both physically and mentally, but it will be a tricky game; they’re friends and it’s difficult for them to play each other.”

Rublev reached his first Grand Slam quarterfinal at the age of 17. This time around, he is 25, and he has plenty more experience and maturity. So far, the World No. 8 has won 14 tour-level titles, including the biggest of his career this year at the Rolex Monte-Carlo Masters.

Now, before another big match, there is no doubt what his mentality and approach to this new challenge will be: it is positive to be back in the quarter-finals of a Grand Slam.

“I don’t see it as negative, it’s positive being in the quarters,” commented Vicente. “If he doesn’t win, we’ll have to try again a 10th time, an 11th… a 22nd. We are delighted to be in the quarters of a Grand Slam again.”

Medvedev leads their Lexus ATP Head2Head 5-2, but Rublev has already taken down his friend on the big stage; last year in the group stage of the Nitto ATP Finals.