Yankees vs. Red Sox Prediction, MLB Picks for Saturday, June 27

First pitch of the matchup between the New York Yankees (48-33) and the Boston Red Sox (34-46) is set for 1:00 p.m. ET on Saturday, June 27, with the Yankees favored and returning a 1.75x payout on PrizePicks Team Picks if they win the matchup on ABC.

This series has already featured some pre-Fourth of July fireworks via a bench-clearing altercation after the Yankees were unhappy with Red Sox 1B Willson Contreras’ bat flip following a walk.

That’s just a culmination of a frustrating series so far for New York. On Thursday, they allowed 6 unearned runs on 4 errors in a 6-3 loss. Then, on Friday, they didn't have a baserunner until the sixth inning in a 6-1 loss. Now, the best the American League East-leading Yankees can do is split the series with the last-place Red Sox.

Below, we'll break down our Yankees vs. Red Sox prediction and picks for Saturday’s MLB matchup, including the run line, over/under, and key player picks for PrizePicks.

Make your Yankees vs. Red Sox prediction and picks on PrizePicks for tonight’s game.

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Yankees vs. Red Sox Prediction, Winner Payout, Over/Under – Saturday, June 27

The Yankees will start SP Gerrit Cole (4.42 xFIP in 32.1 IP, 6 starts) on Saturday. Cole's return from Tommy John surgery started off well, as he resumed his dominant role at the top of the rotation that made him a Cy Young Award winner by pitching 12.2 scoreless innings in his first two starts.

However, as the calendar flipped to June, Cole has struggled to the tune of a 5.95 ERA in 4 starts and is coming off an outing in which he allowed 5 earned runs to the Tigers.

Despite not having key players like DH Giancarlo Stanton, SP Max Fried, and three-time MVP RF Aaron Judge, the Yankees have the best record in the AL. This has much to do with their depth and how their young players are emerging.

1B Ben Rice is becoming one of the top hitters in baseball and is third in the league in OPS (.956), home runs (22), and sixth in wOBA (.405). Starter Cam Schlittler, in just his second year in the league, leads AL pitchers in xERA (2.72), xFIP (2.84), and WAR (3.7).

The Red Sox will counter with SP Jake Bennett (3.42 xFIP in 26.2 IP, 5 starts), who was called up after SP Garrett Crochet went on the injured list. From what the rookie has shown so far, there's optimism that he can become a staple in this rotation.

His changeup is his best pitch because he can get hitters to chase it out of the zone and get swing-and-misses in the zone, as shown by a 35.9% whiff rate. Bennett is seeing success in his young career, allowing 2 or fewer earned runs in three of his five starts.

If the Red Sox can win this four-game series against the Yankees, that might be the highlight of what’s been a failure of a season. Manager Alex Cora was fired after the team started 10-17, and interim manager Chad Tracy is 23-29.

With just a few weeks until the trade deadline, do not be surprised if chief baseball officer Craig Breslow guts this team and sets the foundation of a rebuild.

Yankees vs. Red Sox Winner Payout, Over/Under – Saturday, June 27

The Yankees enter Saturday’s game as road favorites against the Red Sox, returning a 1.75x payout if they win outright, via PrizePicks Team Picks.

Here are the full payouts for the Yankees vs. Red Sox game on PrizePicks.

• Spread: New York Yankees -1.5 (2.22x payout)
• Over/Under: 8.5 (1.85x payout on Over)
• Game Winner Payout: Yankees 1.75x | Red Sox 2x

Play the Yankees vs. Red Sox spread or over/under on PrizePicks Team Picks to earn real money — available in 35 states!

Team Picks data is live at the time of writing and is subject to change.

Yankees vs. Red Sox Prediction on Winner – 6/27/26

Here are the key game stats and trends behind our Yankees vs. Red Sox prediction on the winner for Saturday, June 27.

Lock in your Yankees vs. Red Sox prediction on PrizePicks now.

Unless otherwise noted, data used in this article is from Baseball Savant or FanGraphs.

• The Yankees are successful against left-handed pitching, ranking second in the league with a 19.2 wRAA and a .340 wOBA.
• Cole has struggled at Fenway Park, sporting a 5.52 ERA in 8 starts.
• There's a notable difference between Cole at Yankee Stadium and on the road. He’s been better at home with a 3.12 ERA and an opponent batting average of .177, compared to respective marks of 4.20 and .290 away.
• The Yankees' lineup may be able to counter some of Bennett’s strengths. He’s posting a 40.3% chase rate, which ranks in the 99th percentile, but the Yankees’ 28.3% chase rate is the seventh-lowest in baseball. Bennett also owns a 97th-percentile walk rate (4.7%), but New York boasts a 10.9% mark.
• Cole’s 5 earned runs allowed to the Tigers are his most since September of 2024, when he gave up 7 to the Red Sox.

Yankees vs. Red Sox Picks, Player Stats for PrizePicks: 6/27/26

Here are the top Yankees vs. Red Sox picks to target on Saturday, June 27. Today’s MLB picks for PrizePicks include Paul Goldschmidt and Jarren Duran.

Yankees 1B Paul Goldschmidt vs. Red Sox: 6.5 Hitter Fantasy Score

• Goldschmidt has been locked in recently. Since May 27, he ranks third with 9 home runs, seventh with a .637 SLG, and 13th with a .428 wOBA.
• He is especially dangerous against left-handed pitching, ranking first in SLG (.823), and he's second in the league in BA (.418), wOBA (.553), and wRC+ (262).
• Goldy has a great history at Fenway Park, including a .346 OBP and .333 BABIP.
• Bennett’s strongest pitch is his changeup, allowing a .196 xBA and .194 xSLG. However, Goldschmidt hits it very well, as his .331 xBA is the best. A .562 xSLG is also the second-best against the other eight different pitches he’s seen this year.

Add Paul Goldschmidt to your PrizePicks Lineup now.

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Red Sox LF Jarren Duran vs. Yankees: 5 Hitter Fantasy Score

• Duran has struggled against the Yankees this season, going 7-for-24 (.170 BA). He's just 3-for-17 lifetime against Cole.
• This is the theme of an overall brutal season for Duran, as his .226 xBA, .274 wOBA, and 29.8% strikeout rate are each the second-worst marks of his career.
• His worst regression has come in June, as his .188 wOBA, 21.6% soft contact rate, and -8.7 wRAA are worse than any other month.
• The Red Sox left fielder only has a 38.6% hard-hit rate, slotting into the 38th percentile. Cole has the edge, as his 35.2% hard-hit rate allowed resides in the 72nd percentile.

Add Jarren Duran to your PrizePicks Lineup now.

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It’s not going well for the Yankees during their trip to Fenway. Now, they'll try to salvage a split in the four-game series, with their ace Gerrit Cole trying to rebound after a rough start in Detroit. 

Don’t wait until the first pitch — make your Yankees vs. Red Sox picks on PrizePicks now and earn real money if you’re right.

Pick players, predict More or Less on their stats, and cash in if you’re right. With Team Picks, you can make predictions on game winners, spreads, and over/unders, now available in 35 states.

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