2021 AL Wild Card Game Predictions | Yankees vs Red Sox Best Bets & Projections

Last Updated: Oct 5, 2021

The 2021 AL Wild Card race went down to the wire, remaining undecided until the final day of the regular season. The Boston Red Sox and New York Yankees ultimately emerged from the dogpile, clinching the two Wild Card berths with dramatic victories during Game 162.

While both teams finished the regular season with identical 92-70 records, the Red Sox will host Tuesday’s playoff game at Fenway Park by virtue of winning the season series, 10-9. Boston outscored New York by just one run during their 19 games this year, so these two teams are about as evenly matched as you can get.

Which AL East foe will win in the latest chapter of baseball’s greatest rivalry? Let’s dive in with our Yankees vs Red Sox Wild Card Game predictions and best bets. All Yankees vs Red Sox odds and lines are current as of Tuesday, October 5.

Yankees vs Red Sox AL Wild Card Game Predictions

New York Yankees @ Boston Red Sox, October 5, 8:08 PM EST on ESPN

Probable Starting Pitchers:

  • Gerrit Cole, Yankees (16-8, 3.23 ERA)
  • Nathan Eovaldi, Red Sox (11-9, 3.75 ERA)

As expected, the Yankees will turn to their ace to start this must-win game at Fenway. This is exactly the type of game Gerrit Cole was signed to pitch when New York gave him the largest contract in MLB history for a pitcher two winters ago.

Cole has lived up to those expectations in the first two years of his contract, going 23-11 with a 3.11 ERA, 1.03 WHIP, and 11.9 K/9 rate in 42 regular-season starts for the Yanks. He’s also been a dominant postseason pitcher throughout his career, going 8-4 with a 2.68 ERA and 0.88 WHIP in 13 playoff starts.

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After burning Chris Sale in Game 162, the Red Sox will counter with 2018 World Series hero Nathan Eovaldi. The former Yankee was Boston’s best starter this year en route to his first All-Star nod, leading the AL with a 2.79 FIP and ranking as MLB’s third-most valuable starting pitcher per FanGraphs WAR (5.6).

Similar to Cole, Eovaldi has an outstanding postseason resume. He played an integral role in the Red Sox’s most recent championship, notching a 1.61 ERA and 0.81 WHIP across six appearances during their 2018 title run.

Eovaldi was hammered in his most recent start against the Yankees, getting lit up for seven runs in just 2 2/3 innings at Fenway on September 24. He excelled in his other five starts against them this season with a 1.99 ERA, however, so look for him to bounce back against New York’s feast-or-famine lineup.

As for Cole, he was mediocre in his four starts against the Red Sox this year with a 2-2 record, 4.91 ERA, 1.50 WHIP, and .852 opponent OPS. Those struggles may continue against an offense that ranked fourth in MLB with 5.12 runs per game this year, including a whopping 5.80 at home.

This MLB bet of the day feels like a toss-up. New York could certainly take this one if Giancarlo Stanton and/or Aaron Judge launch a couple of balls over the Green Monster, but Boston seems to have a slight edge given their home-field advantage and Eovaldi’s success against the Yankees this year.

It’ll be close, but I think Boston will squeak out another tight win to advance to the ALDS and face the Tampa Bay Rays.

Yankees vs Red Sox AL Wild Card Pick: Red Sox 4, Yankees 3

Gerrit Cole New York Yankees SP

After leading the AL with 16 wins this year, Gerrit Cole will try to earn another victory over the Boston Red Sox in the 2021 AL Wild Card Game. (Image: USA TODAY Sports)

Yankees vs Red Sox NL Wild Card Game Best Bet

Best Bet: Red Sox 1st 5 Innings Moneyline (+110) at Caesars

Wager: 1 unit

As noted above, the Red Sox have given Cole trouble this year, while Eovaldi was mostly brilliant against the Yankees. Cole also ended the season with a 7.64 ERA and 1.58 WHIP over his final three starts — one of which came at Fenway Park.

I’m not afraid to go against him here, so give me the plus money on Boston at home.

Read all of our 2021 AL Wild Card Game Betting Tips

Best Bet: Under 8 Total Runs (-115) at Caesars

Wager: 1.35 units

If you’re looking to wager on the Total for this MLB pick of the day, SugarHouse has the most favorable lines per our MLB gameday odds.

New York struggled to score against Tampa Bay last weekend, managing just six runs during the three-game series. Boston’s offense has also been quiet lately, averaging 3.9 runs per game over their last nine.

In their 19 head-to-head matchups this season, the two teams averaged 7.84 total runs per game. I expect this to be another low-scoring affair, which is why I’m taking the Under.

Best Bet: Red Sox To Score 1st & Win (+220) at DraftKings

Wager: 0.5 Units

Given Cole’s recent woes, especially against Boston, don’t be surprised if it takes a while for him to settle in. If Eovaldi can get through the top of the first inning unscathed, there’s a good chance the Red Sox jump on Cole in the bottom of the first or soon thereafter.

Boston has one of the more aggressive lineups in baseball, so look for them to come out swinging. They should be able to score before New York’s cold bats and hold on to win the game, making this an attractive MLB prop bet.


Jason Radowitz

Jason Radowitz is a jack of all trades when it comes to writing sports. Jason writes and bets the MLB, NFL, NBA, NCAAF, and NCAAB when the sports are in season. Currently, he's a Writer and Betting Analyst for The Game Day providing daily content in the MLB. Earlier in his sports career, Jason was a graduate assistant for the University of Hartford Men's Basketball team using analytics and numbers to help put together the winningest season in program history. With his articles, you will be sure to get an analytical approach.

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