Red Sox vs Yankees Picks and Predictions: Third Time's the Charm

The Yankees swept a doubleheader against the Red Sox on Tuesday as the AL wild card race heats up. Check out our picks and predictions and find out who we like in Wednesday's rematch in the Bronx.

Andrew Caley - Senior Betting Analyst at
Andrew Caley • Senior Betting Analyst
Aug 18, 2021 • 14:16 ET • 3 min read
Xander Bogaerts Boston Red Sox MLB
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The latest chapter in sport’s greatest rivalry is going to be a doozy. The New York Yankees swept a doubleheader against the hated Boston Red Sox yesterday to pull into a tie for the top wild card spot in the American League.

The Yankees are favored for tonight’s matchup in the Bronx but, the only problem is, they hand the ball to Andrew Heaney who has been giving away home runs like Oprah does cars to a studio audience since donning pinstripes.

Check out our MLB betting free picks and predictions for Red Sox vs. Yankees on Wednesday, August 18.

Red Sox vs Yankees game info

Location: Yankee Stadium, New York, NY
Date: Wednesday, August 18, 2021
Time: 7:05 p.m. ET

Red Sox vs Yankees odds

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Red Sox vs Yankees betting preview

Starting pitchers

Nick Pivetta (9-5, 4.20 ERA): Pivetta has been a pleasant surprise for the Red Sox rotation this season and has bounced back after a bit of a slump. The right-hander has allowed just one run on four hits while striking out 13 in 12 innings of work over his last two starts.

Andrew Heaney (7-8, 5.78 ERA): Heaney has been absolutely lit up since coming over to the Yankees from the Los Angeles Angels at the trade deadline. The lefty is pitching to a 9.00 ERA and 1.40 WHIP over his first three starts in pinstripes but has really had trouble with the long ball, surrendering eight dingers.


Be sure to monitor the gametime conditions with our MLB weather info.

Key injuries

Red Sox: Ryan Brasier RP (Out), Adam Ottavino RP (Out), Matt Carasiti RP (Out).
Yankees: Anthony Rizzo 1B (Questionable), Clint Frazier LF (Out), Gio Urshela 3B (Out), Aroldis Chapman RP (Out), Miguel Andujar LF (Out), Gleyber Torres SS (Out).

Find our latest MLB injury reports.

Betting trend to know

The Over is 14-6-1 in Red Sox's last 21 games as a road underdog. Find more MLB betting trends for Red Sox vs. Yankees.

Moneyline pick

What a turn this epic rivalry has taken this season. The Boston Red Sox lead the American League East for the majority of the first half of the season and took 10 of their 13 games against the rival New York Yankees. 

But, the BoSox are just 6-10 in the month of August after getting swept in yesterday’s doubleheader at Yankee Stadium. The sweep improved the Yanks to 13-4 for the month and pulled them into a tie with the Red Sox for the top spot in the AL wild card race.

The Yankees are hot coming into this matchup, but unfortunately, they hand the ball to Andrew Heaney. The lefty has struggled since joining the Yankees, surrendering 15 runs in 15 innings while allowing opponents to hit .254 with a 1.108 OPS.

Heaney faces a Red Sox team that ranks third in batting average and fifth in OPS when it comes to facing left-handed pitching this season. On the other side, Pivetta is pitching well again and faces a Yankees team that ranks 26th in batting average and 18th in OPS when it comes to facing righties. 

With the Red Sox having the edge in starters they have value as a road underdog in this one.

PREDICTION: Red Sox (+100)

Over/Under pick

When it comes to the total, this AL East matchup hit the board at 9.5 and the early money has come in on the Over, moving the number to an even 10.

While the casual bettor may think the Over is a lock between these rivals, particularly with Heaney on the bump, these games have been tight for the most part, with the Under going an impressive 10-4-1 in their 15 meetings this season. 

While Heaney has his problems, the Yankees’ bullpen is looking strong again, even without Aroldis Chapman. The Yankees relievers rank fourth in ERA and fifth in opponent batting average. In a game with plenty on the line, you can expect manager Aaron Boone to have a short leash with Heaney.

The same can be said for Pivetta and the Red Sox. Bet on another tight game that sneaks below the number.

PREDICTION: Under 10 (-110)

Red Sox vs Yankees betting card

  • Red Sox (+100)
  • Under 10 (-110)

Picks made on 8/18/2021 at 2:00 p.m. ET

MLB parlays

Did you know that if you parlayed today’s MLB Red Sox vs. Yankees picks, you could win $28.18 on a $10 bet?

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