Boston Red Sox vs Chicago Cubs Prediction & Picks - MLB

See our betting tips for the next match between these two teams
Boston Red Sox - Chicago Cubs Betting tips

USA - MLB

Boston Red Sox
9/25/26 13:05
Chicago Cubs

Prediction:

 

Chicago to win

-120
$150 offered for betting!

New customers only | Commercial content | 21+ age limit | T&Cs apply

 by Bill Christy | in MLB Picks

The Chicago Cubs and Boston Red Sox game that was originally scheduled for Sunday has been moved to Friday afternoon and will be the 1st of a double-header. This will begin the final series for each team in the regular season, but both are likely to head to the postseason.

This 4-game series is a bit more meaningful for the Chicago Cubs. They are currently 1 game back of the Padres for the top wild card spot and 1 game ahead of the Phillies for the last wild card spot. Meaning, every game in this 4-game series could shift where the Cubs end up seeded. They will lean on Clay Holmes to start the 1st game of the double-header today. And things have not been great for him lately. He has allowed 17 runs over his last 3 starts and is likely to need heavy run support in this one.

Boston is not in as fluid a spot as the Cubs in terms of their seeding. They are currently 7 games back of the Yankees for the top wild card spot and have a solid 3 game lead on the White Sox for the final spot. They are essentially locked in to that 2nd wild card spot. So, in this opening game, they are opting to have a bullpen start. Reliever Alec Gambos is set to start and likely will pitch just a single inning.

Up to $150 to bet on Boston Red Sox - Chicago Cubs! 

Limited Offer. Currently at DraftKings

Boston Red Sox vs Chicago Cubs Form

Table

Teams Pts P W L
7 Chicago Cubs
0.553 159 88 71
9 Boston Red Sox
0.535 159 85 74

Boston Red Sox and Chicago Cubs Latest Matches

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

2/6 (33%)

Defeats

4/6 (67%)

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

Sep 19, 2026 - MLB

Tampa Bay Rays
2 :  1
Boston Red Sox

Sep 18, 2026 - MLB

Tampa Bay Rays
2 :  4
Boston Red Sox
L W W L W L
Victories

3/6 (50%)

Defeats

3/6 (50%)

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

Sep 12, 2026 - MLB

Boston Red Sox
5 :  1
Kansas City Royals

Sep 11, 2026 - MLB

Boston Red Sox
2 :  3
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
L W 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 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
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 L L W W
Victories

2/6 (33%)

Defeats

4/6 (67%)

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

Sep 8, 2026 - MLB

Milwaukee Brewers
4 :  3
Chicago Cubs

Sep 7, 2026 - MLB

Milwaukee Brewers
4 :  3
Chicago Cubs

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

Boston Red Sox

40 %

Chicago Cubs

60 %

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

Jul 14, 2023 - MLB

Chicago Cubs
3 :  8
Boston Red Sox
Boston Red Sox vs Chicago Cubs Picks

Boston Red Sox - Chicago Cubs Key Points

  1. Boston is 1-4 in their last 5 games.
  2. Boston is 3-5 in their last 8 home games.
  3. Chicago is 2-1 in their last 3 road games.
  4. Chicago is 2-1 in their last 3 games against Boston.
Up to $150 to bet on Boston Red Sox - Chicago Cubs! 

Limited Offer. Currently at DraftKings

Our Boston Red Sox vs Chicago Cubs Prediction

With the Red Sox essentially having nothing to play for and the Cubs fighting for their postseason position, we are backing Chicago. Boston throwing their bullpen in the opener is a sign to us that this could be a throwaway game for them. While Holmes has not been great recently, he is likely to have a short leash as the Cubs will be treating this game as if it’s a playoff game.

Our prediction for Boston Red Sox vs Chicago Cubs: Chicago to win

Prediction:

 

Chicago to win

-120
$150 offered for betting!

A Welcome Bonus for Boston Red Sox vs Chicago Cubs!

DraftKings Welcome Bonus 150

Looking to place a bet on Boston Red Sox vs Chicago Cubs? For this MLB match, DraftKings will treat you to an exclusive offer: $150 in bonus bets, no promo code needed! Take advantage while you still can!

$150 in bonus bets for Boston Red Sox vs Chicago Cubs!

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