Red Sox vs. Brewers
Prediction, Odds & Props
May 27 | MLB AI Picks

Updated: 2025-05-25T03:31:50.923562ZBy Remi at Leans.AI — AI picks for ATS, ML, OU & props

On Tuesday, May 27, 2025, the Boston Red Sox (27–28) will face the Milwaukee Brewers (26–28) at American Family Field in Milwaukee. Both teams are looking to gain momentum as they approach the mid-season mark.

Get key insights, betting trends, and AI-powered predictions to help incorporate into your betting strategies.

AI Sports Betting Algorithm Remi

GAME INFO

Date: May 27, 2025

Start Time: 7:40 PM EST​

Venue: American Family Field​

Brewers Record: (27-28)

Red Sox Record: (27-29)

OPENING ODDS

BOS Moneyline: +100

MIL Moneyline: -120

BOS Spread: -1.5

MIL Spread: +1.5

Over/Under: 8.5

BOS
Betting Trends

  • The Red Sox have a 27–20 record against the spread (ATS) this season, covering the spread in 57.4% of their games.

MIL
Betting Trends

  • The Brewers have a 24–23 record against the spread (ATS) this season, covering the spread in 51.1% of their games.

MATCHUP TRENDS

  • The Red Sox have a +0.5 average margin against the spread, indicating they often outperform expectations.

BOS vs. MIL
Best Prop Bet

  • Remi's searched hard and found the best prop for this matchup: J. Duran over 7.5 Fantasy Score.

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Boston vs Milwaukee Prediction & Odds:
Free MLB Betting Insights for 5/27/25

The Boston Red Sox and Milwaukee Brewers continue their interleague series on Tuesday, May 27, 2025, at American Family Field, with both teams hovering near the .500 mark and looking to build momentum as the season approaches the summer grind. The Brewers came out on top in the series opener with a tight 3–2 victory, showcasing their ability to perform under pressure and execute in low-scoring situations—something they’ve had to rely on throughout a season marked by inconsistency on both sides of the ball. With a 26–28 record, Milwaukee sits just behind the pack in the NL Central and will aim to piece together a win streak to keep pace with division leaders. Their offense has had its struggles, highlighted by the fact that team leader Christian Yelich is hitting just .205 despite leading the club with 9 home runs, but the emergence of young talent like Jackson Chourio, who was recently called up and adds power and energy to the outfield, offers hope for a midseason offensive boost. On the mound, Freddy Peralta has remained a key figure, striking out 60 and helping keep the Brewers competitive in close contests, supported by a team ERA of 4.03 that has been good enough to give them chances most nights. The Brewers’ 15–10 home record suggests a comfort level at American Family Field, and they’ll look to extend that edge against a Boston team trying to find consistency of its own.

The Red Sox, at 27–28, have mirrored Milwaukee in many ways, alternating between offensive outbursts and frustrating dry spells, with a lineup headlined by Rafael Devers (.287 AVG, 10 HR) and Wilyer Abreu (11 HR), both capable of carrying the offense on any given night. Boston’s team ERA also sits at 4.03, and their pitching has been more dependable than expected, led by Garrett Crochet and his team-best 65 strikeouts, but bullpen depth and execution in high-leverage moments remain question marks. Monday’s one-run loss was a tough pill to swallow after generating offensive chances but failing to capitalize in key spots, something they’ll need to clean up if they hope to even the series. Manager Alex Cora has emphasized sharper situational hitting and avoiding defensive lapses, especially in games where the margin is razor-thin and the opposition thrives in close contests. Tuesday’s matchup could easily swing on a few key at-bats, and with both teams needing a win to stabilize their seasons, expect a playoff-like feel to this midweek clash. Boston’s focus will be on getting an early lead to take pressure off the bullpen, while Milwaukee will again look to grind out innings, lean on their pitching, and hope for timely hits from Yelich, Chourio, or a resurgent bat in the bottom half of the order. With similar records, identical team ERAs, and mirrored flaws, this game presents a compelling battle between two squads trying to define themselves in the 2025 playoff picture and find the consistency required to climb their respective divisions.

Boston Red Sox MLB Preview

The Boston Red Sox enter Tuesday’s matchup against the Milwaukee Brewers with a 27–28 record and a sense of urgency after dropping a tight 3–2 decision in the series opener, a game that exposed both their potential and their flaws in a microcosm of their season so far. Boston’s offense generated opportunities but failed to convert in key moments, leaving runners stranded and ultimately falling short in a game decided by small margins—an outcome that has become familiar in 2025. Rafael Devers continues to be the offensive anchor, leading the team with a .287 batting average and 10 home runs while providing left-handed power and leadership in the middle of the lineup. Wilyer Abreu has emerged as another crucial contributor, already launching 11 home runs and offering consistent at-bats that help stretch the lineup beyond just the top three or four hitters. The Red Sox’s offense has not lacked power, but situational hitting and plate discipline have often let them down, especially against quality pitching, which has been a recurring theme on the road where they’ve had trouble manufacturing runs without relying on the long ball. On the pitching side, Boston has been more stable than expected, with a team ERA of 4.03 and a rotation that has quietly held its own in the American League despite lacking big-name aces.

Garrett Crochet has been a key contributor, racking up 65 strikeouts and giving the team consistent innings, and while the bullpen has held up at times, late-inning execution remains an area needing refinement. The Red Sox have a strong 27–20 record against the spread, showing they often perform above market expectations, particularly in close games, and their +0.5 average ATS margin suggests they rarely get blown out even when they lose. Manager Alex Cora will look to clean up the little mistakes that cost them Monday’s game—missed opportunities at the plate, a lack of productive outs, and defensive positioning lapses—while hoping the offense can string together hits more efficiently to support what has been a dependable pitching staff. Boston is capable of going on a run, but inconsistency and lack of rhythm have kept them in a constant cycle of win-one, lose-one, making Tuesday’s matchup critical not just for the series outcome but for setting a more confident tone heading into the next stretch of the season. A win would not only get them back to .500 but also reestablish confidence on the road against a similarly positioned Milwaukee squad. If the Red Sox can get an early lead, minimize bullpen exposure, and deliver in key offensive spots—especially with runners in scoring position—they stand a strong chance of flipping the series and leaving Milwaukee with valuable momentum in the tightly packed AL East.

On Tuesday, May 27, 2025, the Boston Red Sox (27–28) will face the Milwaukee Brewers (26–28) at American Family Field in Milwaukee. Both teams are looking to gain momentum as they approach the mid-season mark. Boston vs Milwaukee AI Prediction: Free MLB Betting Insights for May 27. Credit USA TODAY/IMAGN

Credit: USA TODAY/IMAGN

Milwaukee Brewers MLB Preview

The Milwaukee Brewers head into Tuesday’s contest against the Boston Red Sox with a 26–28 record, looking to string together wins and reignite their push in the NL Central following a much-needed 3–2 victory in the series opener. That win showcased the Brewers’ identity in 2025: gritty, low-scoring, pitching-driven baseball where timely hits and steady bullpen execution make the difference in tight matchups. Christian Yelich remains the team’s marquee name, and although his .205 batting average has yet to match past MVP-level form, he still leads the team in home runs with nine and remains a presence in the lineup who can shift momentum with one swing. The Brewers’ offense overall has struggled to find consistent footing, frequently leaning on small ball and situational hitting to generate runs, and while they’ve managed to stay competitive thanks to discipline at the plate, the lack of consistent power has forced their pitching staff to carry the load. Fortunately for Milwaukee, that pitching staff has delivered a respectable 4.03 team ERA, with Freddy Peralta continuing to anchor the rotation through his 60 strikeouts and ability to pitch deep into games, giving the team much-needed stability. The bullpen has been a strength in close games, as evidenced by Monday’s narrow win, where late-inning composure sealed the outcome and gave the Brewers a win they badly needed to avoid slipping further below .500.

One of the more intriguing storylines this week has been the recent call-up of outfielder Jackson Chourio, whose arrival adds excitement and potential punch to the batting order; his .246 average and nine home runs in the minors suggest there’s pop in his bat, and fans are eager to see if he can spark an offense that has leaned heavily on Yelich and William Contreras. At home, Milwaukee has played better than their overall record suggests, going 15–10 at American Family Field, where the pitching seems more comfortable and the atmosphere gives them a noticeable edge. Manager Pat Murphy has emphasized the need for clean baseball—avoiding unnecessary walks, keeping the defense sharp, and maximizing the few opportunities that arise in pitcher’s duels—and those principles will be critical once again with Boston’s offense looming. To win Tuesday’s game and take control of the series, the Brewers will need to get ahead early, manage pitch counts, and force Boston into defensive mistakes, particularly by applying pressure on the basepaths and getting runners into scoring position with less than two outs. While the margin for error remains small, Milwaukee has proven they can win these tight, grind-it-out games when their pitching and defense are sharp. With the division race tightening and the team still trying to find a rhythm, Tuesday offers another chance to assert themselves at home, keep pace in the NL Central, and show they have the depth and resilience to remain relevant in the playoff picture as summer approaches.

Boston vs. Milwaukee Prop Picks (AI)

AI algorithm Remi is pouring through tons of data on each line. In fact, anytime the Red Sox and Brewers play there’s always several intriguing angles to key in on. Not to mention games played at American Family Field in May almost always follow normal, predictable betting trends.
Remi's searched hard and found the best prop for this matchup: J. Duran over 7.5 Fantasy Score.

Boston vs. Milwaukee Prediction (AI)

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Remi, our AI sports genius, has been pouring over exorbitant amounts of data from every facet between the Red Sox and Brewers and using recursive machine learning and cutting-edge AI to examine the data to a single cover probability.

Remi has been most keyed in on the trending weight knucklehead sportsbettors regularly put on Boston’s strength factors between a Red Sox team going up against a possibly rested Brewers team. In reality, the true game analytics appear to reflect a moderate lean against one Vegas line in particular.

Unlock this in-depth AI prediction and all of our MLB AI picks for FREE now.

Below is our current AI Boston vs Milwaukee picks, computer picks Red Sox vs Brewers, best bets, model edges, confidence ratings.

DATE GAME LEAN %WIN UNITS LEVEL
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These picks update as information changes—injury reports, weather, and market movement. Each line shows our model’s fair price, the edge versus the market, and a unit confidence rating (1–10). Odds and availability vary by sportsbook and time. Edges are computed against the listed price; value may change after line moves. Always shop for the best number. See the full MLB schedule.

Red Sox Betting Trends

The Red Sox have a 27–20 record against the spread (ATS) this season, covering the spread in 57.4% of their games.

Brewers Betting Trends

The Brewers have a 24–23 record against the spread (ATS) this season, covering the spread in 51.1% of their games.

Red Sox vs. Brewers Matchup Trends

The Red Sox have a +0.5 average margin against the spread, indicating they often outperform expectations.

Boston vs. Milwaukee Game Info

Boston vs Milwaukee starts on May 27, 2025 at 7:40 PM EST.

Venue: American Family Field.

Spread: Milwaukee +1.5
Moneyline: Boston +100, Milwaukee -120
Over/Under: 8.5

Boston: (27-29)  |  Milwaukee: (27-28)

Remi's searched hard and found the best prop for this matchup: J. Duran over 7.5 Fantasy Score.. Prices move—always shop for the best number.

The Red Sox have a +0.5 average margin against the spread, indicating they often outperform expectations.

BOS trend: The Red Sox have a 27–20 record against the spread (ATS) this season, covering the spread in 57.4% of their games.

MIL trend: The Brewers have a 24–23 record against the spread (ATS) this season, covering the spread in 51.1% of their games.

See our latest MLB picks and odds pages for 2025 to compare prices before you bet.

Boston vs. Milwaukee Odds

AI algorithm Remi is pouring through loads of data on each team. In fact, anytime the Boston vs Milwaukee trends are analyzed, there’s always several intriguing observations to key in on. Not to mention games played at extreme temps rarely follow normal, predictable betting trends.

Boston vs Milwaukee Opening Odds

BOS Moneyline: +100
MIL Moneyline: -120
BOS Spread: -1.5
MIL Spread: +1.5
Over/Under: 8.5

Boston vs Milwaukee Live Odds

Games PTS ML SPR O/U
In Progress
Baltimore Orioles
New York Yankees
In Progress
Orioles
Yankees
0
3
+950
-2000
+3.5 (+100)
-3.5 (-130)
O 6.5 (-140)
U 6.5 (+105)
In Progress
St Louis Cardinals
Chicago Cubs
In Progress
Cardinals
Cubs
0
0
 
-185
 
-1.5 (+105)
O 9.5 (-125)
U 9.5 (-105)
Sep 27, 2025 3:09PM EDT
Tampa Bay Rays
Toronto Blue Jays
9/27/25 3:09PM
Rays
Blue Jays
+140
-170
+1.5 (-155)
-1.5 (+130)
O 8.5 (-105)
U 8.5 (-115)
Sep 27, 2025 4:05PM EDT
Chicago White Sox
Washington Nationals
9/27/25 4:05PM
White Sox
Nationals
-105
-115
-1.5 (+150)
+1.5 (-180)
O 8.5 (-115)
U 8.5 (-105)
Sep 27, 2025 4:06PM EDT
Colorado Rockies
San Francisco Giants
9/27/25 4:06PM
Rockies
Giants
+190
-235
+1.5 (-105)
-1.5 (-115)
O 8 (-105)
U 8 (-115)
Sep 27, 2025 4:11PM EDT
New York Mets
Miami Marlins
9/27/25 4:11PM
Mets
Marlins
-140
+115
-1.5 (+125)
+1.5 (-150)
O 8 (-105)
U 8 (-115)
Sep 27, 2025 4:11PM EDT
Detroit Tigers
Boston Red Sox
9/27/25 4:11PM
Tigers
Red Sox
+105
-125
-1.5 (+165)
+1.5 (-200)
O 8.5 (-110)
U 8.5 (-110)
Sep 27, 2025 6:05PM EDT
Minnesota Twins
Philadelphia Phillies
9/27/25 6:05PM
Twins
Phillies
+175
-215
+1.5 (-115)
-1.5 (-105)
O 8.5 (-115)
U 8.5 (-105)
Sep 27, 2025 7:11PM EDT
Cincinnati Reds
Milwaukee Brewers
9/27/25 7:11PM
Reds
Brewers
+110
-130
+1.5 (-195)
-1.5 (+160)
O 8 (-110)
U 8 (-110)
Sep 27, 2025 7:15PM EDT
Pittsburgh Pirates
Atlanta Braves
9/27/25 7:15PM
Pirates
Braves
+145
-175
+1.5 (-150)
-1.5 (+125)
O 8 (-105)
U 8 (-115)
Sep 27, 2025 7:16PM EDT
Texas Rangers
Cleveland Guardians
9/27/25 7:16PM
Rangers
Guardians
+120
-145
+1.5 (-190)
-1.5 (+155)
O 7 (-120)
U 7 (+100)
Sep 27, 2025 8:40PM EDT
Arizona Diamondbacks
San Diego Padres
9/27/25 8:40PM
Diamondbacks
Padres
+115
-140
+1.5 (-180)
-1.5 (+150)
O 7.5 (-120)
U 7.5 (+100)
Sep 27, 2025 9:39PM EDT
Houston Astros
Los Angeles Angels
9/27/25 9:39PM
Astros
Angels
-145
+120
-1.5 (+110)
+1.5 (-130)
O 9 (-110)
U 9 (-110)
Sep 27, 2025 9:41PM EDT
Los Angeles Dodgers
Seattle Mariners
9/27/25 9:41PM
Dodgers
Mariners
+100
-120
-1.5 (+175)
+1.5 (-215)
O 7 (-115)
U 7 (-105)
Sep 27, 2025 10:05PM EDT
Kansas City Royals
Oakland Athletics
9/27/25 10:05PM
Royals
Athletics
+100
-120
-1.5 (+150)
+1.5 (-180)
O 10 (-115)
U 10 (-105)

MLB Past Picks

Remi—our in-house AI—prices every game and prop using multi-season priors, tempo/efficiency, injury/usage signals, and market movement.
We publish fair prices, recommended “buy-to” numbers, and confidence so you can bet prices, not teams.

This preview covers Boston Red Sox vs. Milwaukee Brewers on May 27, 2025 at American Family Field.
Odds shown reflect widely available numbers and may update closer to kickoff.

Want more? Check live edges, player props, and line moves on our MLB odds pages, and compare prices before you place a bet.

    LEAN     %WIN     UNITS RESULT
ARI@SD SD -131 57.3% 4 WIN
DET@BOS BOS -115 56.4% 5 WIN
NYM@CHC NYM -110 54.1% 3 WIN
HOU@ATH ATH +118 50.8% 4 WIN
NYM@CHC OVER 7 54.5% 3 WIN
STL@SF OVER 7.5 55.9% 5 LOSS
KC@LAA TYLER TOLBERT UNDER 1.5 BASES 54.4% 4 WIN
MIL@SD UNDER 9 54.7% 4 WIN
MIA@PHI KYLE SCHWARBER OVER 1.5 HITS+RUNS+RBIS 53.3% 3 WIN
WAS@NYM OVER 8.5 56.1% 6 LOSS
LAA@COL COL +108 50.5% 3 WIN
TOR@KC UNDER 9 54.7% 4 LOSS
SEA@KC KC +1.5 62.3% 5 LOSS
NYY@MIN OVER 9 55.1% 4 WIN
MIA@COL OVER 10.5 55.0% 4 WIN
MIA@COL AGUSTIN RAMIREZ OVER 1.5 HITS+RUNS+RBIS 54.3% 4 WIN
SEA@KC BOBBY WITT UNDER 0.5 SINGLES 54.4% 4 LOSS
PHI@LAD LAD -113 54.7% 4 LOSS
NYY@BOS OVER 7.5 54.3% 3 WIN
KC@PHI PHI -130 58.3% 4 WIN
LAD@SF OVER 7.5 54.7% 4 LOSS
NYM@PHI PHI -122 55.6% 4 WIN
KC@CLE KC -104 52.0% 3 WIN
CIN@SD JAKE CRONEWORTH OVER 0.5 HITS 53.1% 3 WIN
WAS@MIA MIA -123 55.2% 4 LOSS
LAA@KC UNDER 9.5 54.9% 3 WIN
TEX@ARI UNDER 9 54.2% 4 WIN
SF@COL UNDER 11.5 56.4% 6 LOSS
SF@COL RAFAEL DEVERS OVER 1.5 BASES 56.1% 6 WIN
MIA@WAS WAS -110 54.4% 4 WIN
NYM@DET OVER 8.5 54.5% 4 WIN
TEX@ARI UNDER 9.5 56.4% 6 WIN
TEX@ARI ALEJANDRO OSUNA UNDER 1.5 BASES 54.1% 4 LOSS
ATL@CHC CHC -116 55.1% 3 WIN
PHI@MIL OVER 8.5 55.0% 3 WIN
ARI@LAD SHOHEI OHTANI OVER 2.5 BASES 54.2% 4 WIN
SEA@CLE CLE +1.5 57.2% 3 WIN
CHC@SF CHC -105 54.1% 4 LOSS
NYY@CHW RYAN MCMAHON OVER 0.5 BASES 54.1% 4 WIN
PHI@NYM OVER 8.5 55.6% 4 LOSS
LAA@TEX LOGAN OHOPPE OVER 1.5 HITS+RUNS+RBIS 54.1% 4 LOSS
KC@CHW KC -109 54.2% 4 WIN
SD@SEA DYLAN CEASE OVER 16.5 OUTS 53.9% 3 LOSS
SD@SEA UNDER 8.5 54.4% 4 LOSS
MIN@TOR JOE RYAN UNDER 2.5 EARNED RUNS 54.1% 4 LOSS
SF@MIL MIL +100 54.0% 6 LOSS
TOR@MIA MIA +1.5 62.0% 6 WIN
CHC@LAA OVER 9.5 54.9% 4 LOSS
BOS@NYY CARLOS RODON UNDER 4.5 HITS ALLOWED 54.2% 4 WIN
KC@DET DET -115 56.1% 5 WIN
CHC@LAA LAA +1.5 57.6% 5 LOSS