Both first and second-round action at the Winston-Salem ATP 250 will take place on Monday, including a battle between Stefanos Tsitsipas and Jenson Brooksby. Cruz Hewitt kicks off his campaign against Sebastian Gorzny.
Jenson Brooksby vs. (7) Stefanos Tsitsipas
Tsitsipas and Brooksby will be going head-to-head for the second time in their careers when they clash in round two of the Winston-Salem Open on Monday. Their only previous encounter came four years ago at the Indian Wells Masters, where Brooksby prevailed 1-6, 6-3, 6-2.
Both players’ careers have been all over the place since that meeting. Although Tsitsipas is far away from his best level, he is showing signs of life this summer. The 49th-ranked Greek won a clay-court title in Gstaad and reached the Montreal third round before falling to Joao Fonseca. Brooksby is also struggling to regain his peak form after missing 2023 and 2024 due to a suspension. The 74th-ranked American is 12-18 on the main tour this season, but he has played better of late and had no trouble beating Giovanni Mpetshi Perricard 6-3, 6-2 on Sunday. Of course, this an entirely different kind of matchup for Brooksby — one that will likely be too difficult.
Pick: Tsitsipas in 2
(LL) Sebastian Gorzny vs. (WC) Cruz Hewitt
Hewitt is starting to make a name for himself in tennis, beyond simply being Lleyton’s son. The 17-year-old Australian finished runner-up in the Wimbledon boys singles event a month ago and played his first tour-level event in Washington, D.C., where he qualified for the main draw and upset Marcos Giron before succumbing to Alex de Minaur 6-2, 6-3.
Up first for Hewitt in Winston-Salem on Monday is Gorzny, who is coming off a decorated college career at TCU and Texas. The 22-year-old American lost in qualifying on Sunday, but at least he already has two matches under his belt and is accustomed to the conditions at this tournament. Gorzny has been among the very best college players over the past couple of years. Would Hewitt be in that group if he went to college right now? Probably not.
Pick: Gorzny in 3


WWW?
I doubt young Hewitt will beat your college dude; your reasons plus Gorzny is taller, stronger, not a puppy anymore. If he’s lucky Hewitt will steal a set. He’s not an early developer like his Dad or Nadal or Alcaraz and IMO won’t get near their heights either. He’s been over-hyped and was given far better opportunities than more talented young Australian players because the family has money and tennis connections that the kids of scrabblers simply don’t. So there’s my view as an Aussie. I’m happy to be proven wrong.
And just because I think Brooksby is a quality player who’s beaten Tsitsipas before and taken out some good quality players this year, and because Tsitsipas can be so easily rattled, and because Brooksby is playing at home with crowd support, I’m taking the view that Brooksby will beat Tsitsipas here.
Haha! Wrong on both. And I’ll jinx myself if I say I still don’t think either will get very far in this tournament.
Fery will definitely be up in class though. Unless he was a Lleyton devotee growing up and gets funny about the meeting.