Boston Red Sox vs Chicago Cubs Prediction & Picks - MLB

USA - MLB

Boston Red Sox
9/27/26 15:05
Chicago Cubs

Prediction:

 

Boston ML

+106
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 by Travis Pulver | in MLB Picks

The Boston Red Sox (87-74, 41-39 Home) will look to end the regular season at home in style with a sweep of the Chicago Cubs (88-73, 42-38 Away). This game was originally scheduled for Saturday but was postponed to today and moved to Tropicana Field in St. Petersburg, FL, due to inclement weather.

First Pitch is scheduled for 3:05 p.m. EST, with coverage provided by MLB.TV.

Predicting the outcome of this game is a bit more challenging than usual because we do not have some pretty important information. Neither team has announced who will start the game on the mound. Both teams are already locked into their postseason matchup. The Red Sox will face the Yankees in the Wild Card round, and the Cubs are taking on the Padres. Consequently, I wouldn’t expect either team to put its best foot forward with a starter, or if they opt for a bullpen day.

A bullpen day would definitely benefit the Red Sox, whose bullpen has the lowest ERA in baseball this season at 2.99. It has a cumulative WHIP of 1.17, and teams have hit .224 against the Boston pen. As for the Cubs, Chicago’s bullpen has a 3.93 ERA, 1.29 WHIP, and teams have hit .242 against it this season.

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Boston Red Sox vs Chicago Cubs Form

Table

Teams Pts P W L
7 Chicago Cubs
0.549 162 89 73
9 Boston Red Sox
0.537 162 87 75

Boston Red Sox and Chicago Cubs Latest Matches

Boston Red Sox
Boston Red Sox Latest matches
L L W L W W
Victories

3/6 (50%)

Defeats

3/6 (50%)

Sep 25, 2026 - MLB

Boston Red Sox
2 :  0
Chicago Cubs

Sep 25, 2026 - MLB

Boston Red Sox
4 :  3
Chicago Cubs

Sep 24, 2026 - MLB

Boston Red Sox
0 :  1
Cleveland Guardians

Sep 23, 2026 - MLB

Boston Red Sox
1 :  0
Cleveland Guardians

Sep 22, 2026 - MLB

Boston Red Sox
2 :  3
Cleveland Guardians

Sep 20, 2026 - MLB

Tampa Bay Rays
5 :  1
Boston Red Sox
W L W L W W
Victories

4/6 (67%)

Defeats

2/6 (33%)

Sep 25, 2026 - MLB

Boston Red Sox
2 :  0
Chicago Cubs

Sep 25, 2026 - MLB

Boston Red Sox
4 :  3
Chicago Cubs

Sep 24, 2026 - MLB

Boston Red Sox
0 :  1
Cleveland Guardians

Sep 23, 2026 - MLB

Boston Red Sox
1 :  0
Cleveland Guardians

Sep 22, 2026 - MLB

Boston Red Sox
2 :  3
Cleveland Guardians

Sep 13, 2026 - MLB

Boston Red Sox
4 :  1
Kansas City Royals
L L W W L L
Victories

2/6 (33%)

Defeats

4/6 (67%)

Sep 20, 2026 - MLB

Tampa Bay Rays
5 :  1
Boston Red Sox

Sep 19, 2026 - MLB

Tampa Bay Rays
2 :  1
Boston Red Sox

Sep 18, 2026 - MLB

Tampa Bay Rays
2 :  4
Boston Red Sox

Sep 17, 2026 - MLB

Texas Rangers
3 :  4
Boston Red Sox

Sep 16, 2026 - MLB

Texas Rangers
7 :  3
Boston Red Sox

Sep 15, 2026 - MLB

Texas Rangers
4 :  2
Boston Red Sox
Chicago Cubs
Chicago Cubs Latest matches
W L L W L L
Victories

2/6 (33%)

Defeats

4/6 (67%)

Sep 25, 2026 - MLB

Boston Red Sox
2 :  0
Chicago Cubs

Sep 25, 2026 - MLB

Boston Red Sox
4 :  3
Chicago Cubs

Sep 24, 2026 - MLB

Chicago Cubs
2 :  1
Miami Marlins

Sep 23, 2026 - MLB

Chicago Cubs
2 :  3
Miami Marlins

Sep 22, 2026 - MLB

Chicago Cubs
2 :  8
Miami Marlins

Sep 20, 2026 - MLB

Cincinnati Reds
1 :  9
Chicago Cubs
W L W L L W
Victories

3/6 (50%)

Defeats

3/6 (50%)

Sep 24, 2026 - MLB

Chicago Cubs
2 :  1
Miami Marlins

Sep 23, 2026 - MLB

Chicago Cubs
2 :  3
Miami Marlins

Sep 22, 2026 - MLB

Chicago Cubs
2 :  8
Miami Marlins

Sep 16, 2026 - MLB

Chicago Cubs
8 :  4
Atlanta Braves

Sep 15, 2026 - MLB

Chicago Cubs
3 :  6
Atlanta Braves

Sep 14, 2026 - MLB

Chicago Cubs
7 :  3
Atlanta Braves
L L W W L L
Victories

2/6 (33%)

Defeats

4/6 (67%)

Sep 25, 2026 - MLB

Boston Red Sox
2 :  0
Chicago Cubs

Sep 25, 2026 - MLB

Boston Red Sox
4 :  3
Chicago Cubs

Sep 20, 2026 - MLB

Cincinnati Reds
1 :  9
Chicago Cubs

Sep 19, 2026 - MLB

Cincinnati Reds
2 :  5
Chicago Cubs

Sep 18, 2026 - MLB

Cincinnati Reds
6 :  4
Chicago Cubs

Sep 9, 2026 - MLB

Milwaukee Brewers
8 :  6
Chicago Cubs

Boston Red Sox against Chicago Cubs : Head to Head (H2H)

Boston Red Sox

50 %

Chicago Cubs

50 %

Sep 25, 2026 - MLB

Boston Red Sox
2 :  0
Chicago Cubs

Sep 25, 2026 - MLB

Boston Red Sox
4 :  3
Chicago Cubs

Jul 19, 2025 - MLB

Chicago Cubs
6 :  0
Boston Red Sox

Jul 18, 2025 - MLB

Chicago Cubs
4 :  1
Boston Red Sox

Apr 27, 2024 - MLB

Boston Red Sox
17 :  0
Chicago Cubs

Apr 26, 2024 - MLB

Boston Red Sox
1 :  7
Chicago Cubs
Boston Red Sox vs Chicago Cubs Picks

Boston Red Sox - Chicago Cubs Key Points

  1. Boston went 10-13 in games after a day off this season; Chicago went 9-11.
  2. Boston went 12-11 ATS (run line) after a day off; Chicago went 6-14 ATS (run line).
  3. The OVER went 8-15 for Boston after a day off and 11-9 for the Cubs.
  4. Betting Public: 34% of moneyline tickets and 74% of the handle are on Boston.
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Our Boston Red Sox vs Chicago Cubs Prediction

I can’t see any reason for the public to back the Cubs as much as it is (66% of moneyline bets, 65% of run line bets, and 78% of the handle). It’s not like the Cubs need the win more than Boston; neither team actually needs it. Both teams have been lackluster at the plate in this series, but the Red Sox have done enough to find a way to win both games. Because of that and since the Red Sox are +106 to win at home, I’m backing Boston for this game.

Our Chicago vs. Boston Pick: Red Sox ML

Prediction:

 

Boston ML

+106
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All tips are fully researched and given in good faith, but profits cannot be guaranteed.