Tsitsipas Survives Three Match Points to Advance in Winston-Salem

A Win That Nearly Got Away

It should have been comfortable. Stefanos Tsitsipas, seventh seed at the 2026 Winston-Salem Open, faced Jenson Brooksby in the second round on Monday — and with the Greek leading 5-4 in the second set, holding three match points, the match appeared to be heading to a routine conclusion. It was not.

Brooksby, a 25-year-old American known for his unorthodox, slice-heavy game, saved all three and pushed the set into a tiebreak. There, he found another gear: at 5-6 in the breaker, he held a set point that would have levelled the match. Tsitsipas saved it, then won the tiebreak 7-6 and with it the match, 6-4, 7-6(6), in one hour and 40 minutes. The scoreline gives nothing away about the turbulence inside it.

One statistic explains why Tsitsipas ultimately prevailed despite the anxiety of the closing stretch: he saved seven of the eight break points he faced across the match. When the moment truly required it, his serve held.

Mindset as the Deciding Factor

"Mindset matters," Tsitsipas said in his post-match remarks. "Everyone can play good tennis, everyone can hit the ball. But when the moment gets crucial, when you have to really step up, I feel like mindset is the only thing that helps."

The statement carries weight coming from a player whose career has been shaped as much by mental moments as by technical gifts. Now 28, Tsitsipas has reached five Grand Slam finals and was once ranked as high as No. 3 in the world. He has had matches where the pressure proved decisive in both directions — Monday in Winston-Salem fell, narrowly, on the right side.

The win levelled his ATP Head-to-Head record against Brooksby at 1-1. The American had been in excellent form all week; he dismantled Giovanni Mpetshi Perricard 6-3, 6-2 in the first round before taking Tsitsipas as deep as he did. For Brooksby, the near-miss will be difficult to absorb.

The Winston-Salem Picture

The Winston-Salem Open is an ATP 250 event at Wake Forest University in North Carolina and serves as the final meaningful tune-up before the US Open main draw begins on August 30. The field is headlined by top seed Daniil Medvedev, whose first match of the week — against wild card Martin Damm — is scheduled for Tuesday evening. Second seed Luciano Darderi also advanced on Monday, beating Mattia Bellucci 2-6, 6-4, 6-2 in a three-setter.

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Fourth seed Arthur Fery, the young Frenchman who has emerged as a genuine force on the ATP 250 circuit this year, is also scheduled to play Tuesday, meeting 17-year-old wild card Cruz Hewitt — son of Australian great Lleyton Hewitt. Hewitt's presence in the draw has been one of the more talked-about storylines of the week.

Context Heading Into the US Open

For Tsitsipas, Winston-Salem is about more than the title. Results here help calibrate form and seeding expectations heading into Flushing Meadows. With Jannik Sinner having withdrawn from the US Open due to a knee injury last week — handing the top-seeding to Alexander Zverev — the draw has opened up in a way that benefits several players who might otherwise have faced the Italian. Tsitsipas, if he can build on Monday's result, enters the US Open in a stronger position than recent seasons suggested he would. His next match in Winston-Salem will determine whether that momentum is real.

Corrected on 4 October 2026: result amended.