Jenson Brooksby vs. Stefanos Tsitsipas Prediction, Betting Pick, Latest ATP Winston-Salem Odds - Monday, August 24th
Jenson Brooksby will face seventh-seeded Stefanos Tsitsipas in the second round of the Winston-Salem Open on Monday, August 24. Tsitsipas enters as the favorite, but Brooksby brings a favorable head-to-head history into one of the most intriguing matches of Monday night's schedule.
Peter Alexis - August 24, 2026, 4:00 PM EDT
4 Minute ReadJenson Brooksby vs. Stefanos Tsitsipas Prediction: Can Brooksby Upset Tsitsipas on Monday Night in ATP Winston-Salem?
Brooksby and Tsitsipas are scheduled for a 6:30 PM ET start on Stadium Court at Wake Forest University, with Tsitsipas priced at -162 and Brooksby available as a +132 underdog. Tsitsipas enters the tournament ranked No. 49 in the world, while Brooksby sits at No. 74.
The market is still giving plenty of respect to Tsitsipas' pedigree as a former World No. 3, but his recent hard-court results have not matched the price. Brooksby, meanwhile, already has a match under his belt in Winston-Salem and looked significantly sharper in his opening-round victory.
Jenson Brooksby vs. Stefanos Tsitsipas Odds
- Moneyline: Brooksby (+132), Tsitsipas (-165)
Jenson Brooksby vs. Stefanos Tsitsipas Date, Time, and Where to Watch
- Date: Saturday, August 22nd, 2026
- Time: 6:00 PM ET
- Where to Watch: Tennis Channel
Click here for complete Jenson Brooksby vs. Stefanos Tsitsipas Odds
Jenson Brooksby vs. Stefanos Tsitsipas Prediction
Brooksby needed exactly one hour to dismantle Giovanni Mpetshi Perricard 6-3, 6-2 on Sunday. The American broke the massive-serving Frenchman four times and consistently neutralized one of the biggest weapons on tour with his return game. That performance was particularly encouraging after Brooksby had suffered early exits in both Montreal and Cincinnati earlier this month.
There is also meaningful history behind the upset case. Brooksby and Tsitsipas have met once before, with Brooksby stunning the Greek 1-6, 6-3, 6-2 at Indian Wells in 2022. Tsitsipas dominated the opening set before Brooksby's awkward timing, defense and ability to extend rallies completely changed the match. Those same traits remain capable of frustrating Tsitsipas when his baseline game is not at its best.
Tsitsipas appeared to have finally rediscovered his momentum earlier this summer when he won the Gstaad title, his first ATP Tour trophy in nearly 17 months. That run came on clay, however, and the momentum has faded since returning to hard courts. Tsitsipas lost his Washington opener to Alex de Minaur, beat Martin Damm Jr. before losing in straight sets to Joao Fonseca in Montreal, then followed a win over Valentin Royer in Cincinnati with another straight-set defeat against Felix Auger-Aliassime.
That leaves Tsitsipas without consecutive main-draw hard-court victories since the summer swing began. Even his 7-6, 7-5 win over Royer in Cincinnati became uncomfortable after Tsitsipas surrendered a 5-2 second-set advantage. He is still the more accomplished player, but the current version of Tsitsipas does not warrant automatically laying a sizable moneyline against an opponent who has already shown he can disrupt him.
Jenson Brooksby vs. Stefanos Tsitsipas Best Bet
- Best Bet: Brooksby Moneyline (+132) Check out the best odds at DraftKings Sportsbook
Brooksby comes into Monday with immediate confidence, a stylistically uncomfortable game and the only head-to-head victory between these players. At +132, there is enough value to back the American to reproduce the matchup problems he created four years ago and take advantage of Tsitsipas' fading summer form.
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