Logo

Commercial Content, 21+

Action Network

Get the free Action Network app for expert picks, live odds, bet tracking and more.

This weekend’s series between the New York Yankees and Boston Red Sox has a different kind of feel to it. Of course, anytime these eternal rivals meet it will get tongues wagging – especially when they’re first and second in the division – but the gulf between Boston and New York is so wide right now that these games just don’t pack the usual pizzazz. That said, a strong showing from the Red Sox over the next 10 days — during which the Yanks and Sox will play seven times — could create some drama in the AL East.

A win on Thursday night – the first game between these two teams since the season-opening series – would be a good start for the Red Sox. Unfortunately for them, bookmakers have the Yanks as -178 favorites at Fenway Park.

Those odds could seem a bit jarring given that this is a rivalry game and the Red Sox are at home, but the pitching matchup severely favors the Yankees with Gerrit Cole taking on 24-year-old rookie Josh Winckowski. 

Yankees vs. Red Sox odds

Odds provided by Caesars Sportsbook

Spread: NYY -1.5 (-105) vs. BOS +1.5 (-115)

Moneyline: NYY (-170) vs. BOS (+143)

Total: Over 9 (-105) | Under 9 (-115)

Bet $20 Get $100 in Bonus Bets!
New WynnBet users only. Must be 21+. Offer available in AZ, CO, IN, LA, MI, NJ, NY, TN, VA only. Full Terms and Conditions Apply.

Caesars Sportsbook Logo Square
Up to $1,250 First Bet on Caesars with code NPBONUSFULL
New players only, 21+. Available in AZ, CO, IA, IL, PA, IN, KS, LA, MI, NJ, NY, TN, VA, WV only. Full Terms and Conditions apply.

Bet $1, Get $200 in Bonus Bets
New players only, 21+. Gambling Problem? Call 1-800-GAMBLER. Available in NJ, CO, VA, OH only. Deposit required. Bonus Bets added to Bonus Bets balance. Bonus Bets risk excluded from returns. Terms and Conditions, time limits and exclusions apply.

The BetRivers Logo
2nd Chance Bet up to $500 with code NYPBONUS
New players only, 21+. Available in AZ, CO, IA, IL, IN, LA, MI, NJ, PA, VA only. In order to participate in this promotion, the player needs to make a first deposit (of at least $10). Full Terms and Conditions apply.

The BetRivers Logo
2nd Chance Bet up to $100 with code NYPBONUS
New players only, 21+. Available in NY only. In order to participate in this promotion, the player needs to make a first deposit (of at least $10). Full Terms and Conditions apply.

betPARX
Bet $10, Get $125 in Sports Bonus if your first bet wins
Gambling Problem? Call 1-800-GAMBLER. Must be 21+ and located in PA or NJ. New users & winning bets only. Terms and Conditions apply. See website for details.

100% match up to $500
Claim your eligible bonus from within account after login per promotion instructions. Either way, get a 100% match up to $250 on your first deposit. Only one code may be used. First Deposit Bonus may only be claimed once per person. Must be 21+. CT only. Full Terms and Conditions apply.

Bet $10, Get $125 If Your Bet Wins!
New users only, 21+. Available in MI only. Full Terms and Conditions apply.


  Josh Winckowski. Getty Images Josh Winckowski. Getty Images

Yankees vs. Red Sox MLB pick

While Winckowski’s surface-level numbers – he’s got a 3.12 ERA and 1.38 WHIP in 26 innings – are impressive for a debutante, he hasn’t faced an elite offense like the Yankees just yet. His five outings this season came against the White Sox, Orioles, A’s, Guardians and Tigers. 

So far, Winckowski profiles as a pitcher who relies on his ability to induce weak contact rather than rack up the strikeouts. The former 15th-round pick has punched out 19 batters in 26 innings, which isn’t eye-popping but will play when you blend in his 56.1% ground ball rate and 0.35 HR/9. 

Winckowski will have his work cut out for him not only against the Yankee offense, but he’ll need to keep pace with Gerrit Cole. And even though Cole has had his struggles in Beantown and is a better pitcher at home than on the road, his overall body of work this season sparkles. Cole owns a 2.99 ERA and 1.01 WHIP through 93.1 innings of work and his peripheral numbers (2.99 xERA and 2.89 xFIP) show that he’s earned every bit of his statline this season.


  Gerrit Cole Getty Images Gerrit Cole Getty Images

Betting on Baseball?

The Red Sox caught fire in June, winning 20 of 26 games, to get themselves back into the playoff chase. But Yankees basically answered them every step of the way. New York is just at a different level compared to its longtime rival right now. 

With an offense that hasn’t been stopped all season and a pitching matchup that could turn ugly, the Yankees make a good candidate for a bet on the alternate runline on Thursday night.

Yankees vs. Red Sox pick

Alternate spread – Yankees -2.5 (+140) via Caesars Sportsbook

Comments
anonymous profile image
Powered by RoundtableBuilt on infrastructure designed for real-time media. Learn more at RTB.io.© Roundtable 2026. By using this site you agree to the Terms of Use and Privacy Policy