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Brooksby vs Tsitsipas Odds Preview and Winston-Salem Best Bet

Brooksby owns the head-to-head edge entering his match with Tsitsipas.

(Photo by Getty Images) Stefanos Tsitsipas
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Brooksby vs Tsitsipas Winston-Salem Open Matchup

Matchup: Jenson Brooksby vs (7) Stefanos Tsitsipas
When:  Aug 24 2026, 6:30 PM
Tournament:  Winston-Salem Open
Round:  Round of 32
Venue: Wake Forest University
Location: Winston-Salem, North Carolina

Jenson Brooksby vs Stefanos Tsitsipas
Game Spread

Jenson Brooksby   2.5 (-120)
Stefanos Tsitsipas   -2.5 (-110)

Jenson Brooksby vs Stefanos Tsitsipas
Moneyline

Jenson Brooksby   +130
Stefanos Tsitsipas   -155

Jenson Brooksby vs Stefanos Tsitsipas
Total

Over   22.5 (-110)
Under   22.5 (-120)

(Get real-time live scores & latest betting odds here!)

Brooksby vs Tsitsipas ATP Tennis Preview

Jenson Brooksby and Stefanos Tsitsipas meet Monday in the second round of the Winston-Salem Open, offering bettors an intriguing matchup between contrasting form. Brooksby looked sharp in his opener, dismissing Giovanni Mpetshi Perricard 6-3, 6-2 in just 60 minutes while breaking the powerful Frenchman four times.

Tsitsipas enters as the No. 7 seed after receiving a first-round bye, but his recent hard-court inconsistency creates betting concerns. Brooksby also owns a 1-0 head-to-head advantage, rallying past Tsitsipas 1-6, 6-3, 6-2 at Indian Wells in 2022. Current momentum makes the American a dangerous betting option.

Brooksby vs Tsitsipas Matchups Props

Jenson Brooksby vs Stefanos Tsitsipas
Game Spread

Jenson Brooksby – S1   1.5 (-130)
Stefanos Tsitsipas – S1   -1.5 (EVEN)

Jenson Brooksby vs Stefanos Tsitsipas
Moneyline

Jenson Brooksby – S1   +120
Stefanos Tsitsipas – S1   -155

Jenson Brooksby vs Stefanos Tsitsipas
Total

Over – S1   10.5 (+220)
Under – S1   10.5 (-300)

Jenson Brooksby vs Stefanos Tsitsipas
Alternate Total Games

Over   20.5 (-185)
Under   20.5 (+140)
Over   21.5 (-150)
Under   21.5 (+115)
Over   22.0 (-125)
Under   22.0 (-105)
Over   23.0 (+105)
Under   23.0 (-135)
Over   23.5 (+115)
Under   23.5 (-150)
Over   24.5 (+110)
Under   24.5 (-145)

Jenson Brooksby vs Stefanos Tsitsipas
Alternate Total Games

Over – S1   8.5 (-485)
Under – S1   8.5 (+320)
Over – S1   12.5 (+340)
Under – S1   12.5 (-525)

Jenson Brooksby vs Stefanos Tsitsipas
Total Games O/U – Jenson Brooksby

Over   12.5 (+115)
Under   12.5 (-150)

Jenson Brooksby vs Stefanos Tsitsipas
Total Games O/U – Stefanos Tsitsipas

Over   12.5 (-125)
Under   12.5 (-105)

Jenson Brooksby vs Stefanos Tsitsipas
Total Games O/U

Over – S1   9.5 (-130)
Under – S1   9.5 (EVEN)

Jenson Brooksby vs Stefanos Tsitsipas
Alternate Game Spread

Jenson Brooksby   1.5 (+105)
Stefanos Tsitsipas   -1.5 (-135)
Jenson Brooksby   2.0 (-110)
Stefanos Tsitsipas   -2.0 (-120)
Jenson Brooksby   3.0 (-150)
Stefanos Tsitsipas   -3.0 (+115)
Jenson Brooksby   3.5 (-175)
Stefanos Tsitsipas   -3.5 (+135)
Jenson Brooksby   4.5 (-250)
Stefanos Tsitsipas   -4.5 (+185)

Jenson Brooksby vs Stefanos Tsitsipas
Alternate Game Spread

Jenson Brooksby – S1   -1.5 (+175)
Stefanos Tsitsipas – S1   1.5 (-230)

Jenson Brooksby vs Stefanos Tsitsipas
Set Betting

Jenson Brooksby 2 – 0   +275
Jenson Brooksby 2 – 1   +385
Stefanos Tsitsipas 2 – 0   +142
Stefanos Tsitsipas 2 – 1   +290

Jenson Brooksby vs Stefanos Tsitsipas
Set Spread

Jenson Brooksby   1.5 (-200)
Stefanos Tsitsipas   -1.5 (+150)

Jenson Brooksby vs Stefanos Tsitsipas
Alternate Set Spread

Jenson Brooksby   -1.5 (+275)
Stefanos Tsitsipas   1.5 (-400)

Jenson Brooksby vs Stefanos Tsitsipas
Total Sets

Over   2.5 (+140)
Under   2.5 (-185)

Jenson Brooksby vs Stefanos Tsitsipas
Set Correct Score

Stefanos Tsitsipas – 6 – 0 – S1   +4500
Stefanos Tsitsipas – 6 – 1 – S1   +1100
Stefanos Tsitsipas – 6 – 2 – S1   +750
Stefanos Tsitsipas – 6 – 3 – S1   +390
Stefanos Tsitsipas – 6 – 4 – S1   +475
Stefanos Tsitsipas – 7 – 6 – S1   +600

Jenson Brooksby vs Stefanos Tsitsipas
Tiebreak In Set

Yes – S1   +320
No – S1   -485

Jenson Brooksby vs Stefanos Tsitsipas
Will there be a tie-break in the match?

Yes   +145
No   -190

Jenson Brooksby vs Stefanos Tsitsipas
Odd/Even Total Games

Even   -110
Odd   -110

Jenson Brooksby vs Stefanos Tsitsipas
Will Jenson Brooksby Win At Least One Set?

Yes   -200
No   +150

Jenson Brooksby vs Stefanos Tsitsipas
Will Stefanos Tsitsipas Win At Least One Set?

Yes   -400
No   +275

Winston-Salem Open ATP Tennis Predictions

Tennis Pick: Alternate Total Games – Over 23.0 (+105)
A $100 Bet on that Props will return $205

Tennis Odds & Props source: Bovada Sportsbook

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