Red Sox vs Yankees Prediction, Picks & Odds — Thursday, August 21

Hatfield's prediction: Aaron Judge and the Yankees have struggled against Lucas Giolito and the Red Sox, but they'll look to turn the tide tonight.

Chris Hatfield - Contributor at Covers.com
Chris Hatfield • Betting Analyst
Aug 21, 2025 • 16:10 ET • 4 min read

MLB

Match starts: 1 hrs
NYY
51 %
BOS
49 %
EXPERT PICK - PROP
Aaron Judge o1.5  Total Bases (-110) Aaron Judge o1.5 Total Bases (-110)
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Aaron Judge New York Yankees MLB
Photo By - Imagn Images. New York Yankees right fielder Aaron Judge (99) smiles after a base hit.

In what amounts to one of the biggest series of the year for each team, the Boston Red Sox and New York Yankees will renew their rivalry in New York tonight.

To put it plainly, Boston has owned this series in recent meetings with five straight wins.

Can the Yankees slow that momentum and add some validity to their recent win streak?

My Red Sox vs. Yankees predictions break it all down as I expect Aaron Judge to make a big impact in our MLB picks for Thursday, August 21.

Red Sox vs Yankees prediction

Red Sox vs Yankees best bet: Aaron Judge Over 1.5 total bases (-105)

The dynamic I’ve talked about for the last week is in play here tonight. The New York Yankees will face a pitcher in Lucas Giolito with a barrel rate in the bottom 25% of baseball who throws the fastball over 40% of the time.

In the past, this has been a signal and a system to bet the Yankees to score a good number of runs. However, tonight is a bit complicated.

Up to 20 MPH winds are expected to blow in this evening at Yankee Stadium, which will greatly reduce ball carry and thus make Giolito’s issues less exploitable.

While I’m pausing on the team's total aspect of things because of this, I’m not totally skipping the fade of him. I’m going to head to the prop market and take Aaron Judge Over 1.5 bases for tonight's best bet.

Judge fits here in every way except head-to-head history against Giolito, where he has been 0-4 in his career. Important context is needed though. Much of those meetings came at the prime of Giolito’s career and not who he is now.

What he is now is a pitcher with a barrel rate and hard-hit rate that are anemic, and a guy who loves to throw high-velocity stuff. You simply can’t ask for a better matchup—granted he gets some competitive pitches.

Red Sox vs Yankees same-game parlay (SGP)

We’re pairing Jarren Duran to get an RBI with our best bet.

He’ll benefit from his placement in the lineup but also the pitching arsenal he’ll see. He ranks in the top three of hard-hit rate among Boston Red Sox players against any pitch he’ll see. 

Bet on him to make an impact even if the Yankees pull out the win. 

Red Sox vs Yankees odds

  • Moneyline: Boston -120 | New York +100
  • Run line: Boston +1.5 (-200) | New York -1.5 (+164)
  • Over/Under: Over 8.5 | Under 8.5

Red Sox vs Yankees trend

The New York Yankees have hit the Game Total Over in 27 of their last 42 games (+12.45 Units / 27% ROI). Find more MLB betting trends for Red Sox vs. Yankees.

How to watch Red Sox vs Yankees and game info

Location Yankee Stadium, Bronx, NY
Date Thursday, August 21, 2025
First pitch 7:15 p.m. ET
TV FOX
Red Sox starting pitcher Lucas Giolito
(8-2, 3.63 ERA)
Yankees starting pitcher Luis Gil
(1-1, 5.14 ERA)

Red Sox vs Yankees latest injuries

Red Sox vs Yankees weather

Odds are correct at the time of publishing and are subject to change.
Not intended for use in MA.
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Chris Hatfield - Covers.com
Betting Analyst

Chris has always had a passion for three things: solving problems, sports, and writing. It’s no wonder then that he found himself attracted to the sports betting industry. You can find Chris betting every day. Whether it’s shot prop markets in Champions League Soccer qualifiers or NBA Summer League, he has no offseason. As an EV+ bettor, he especially values the insight gained through a data-driven approach.

His work has been featured on various websites such as SBNation, Rivals, Bleacher Report, and 247Sports. He has appeared on radio outlets such as ESPN 680 and The Sharp 600 podcast. You can listen to his own podcast, “What High School Did You Go To?” on Apple Podcast and Soundcloud.

Chris has carved out a niche as a college basketball originator with massive profitability success in that sport and stresses one piece of advice to sports bettors: exploit edges as broadly as possible and take advantage of them while they last. His preferred sportsbook is bet365 because of the range of markets you can find.

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