Preview·3:05 PM EDT·Fenway Park

Cubs vs Red Sox Prediction, Picks, Best Bets & Parlay

Free MLB prediction and picks for Sunday, September 27, 2026 · powered by DataStreak

AWAY

Chicago Cubs

87-69 · W2

HOME

Boston Red Sox

84-72 · L2

Cubs vs Red Sox Prediction

Mid-season MLB matchup, no playoff implications, no marquee narrative. Just two teams and a slate of player props worth looking at.

Prop angles are where the edge lives. Live odds, current streaks, and the picks our partner DataStreak likes are all below.

Cubs vs Red Sox Picks

Books have not posted player props for CHC at BOS yet. Lines usually go up a few hours before first pitch or tip-off; check back closer to game time. See all of today’s free picks across the slate.

Injury Report

26 listed

JUST IN: Ben Brown 15-day-il → 60-Day IL (Neck) · Phil Maton 15-day-il → 60-Day IL (Knee) · Riley Martin 15-day-il → 60-Day IL (Elbow) · Cade Horton 15-day-il → 60-Day IL (Elbow) · Porter Hodge 15-day-il → 60-Day IL (Elbow) · Hunter Harvey 15-day-il → 60-Day IL (Triceps) · Trent Thornton paternity → 15-Day IL (Ankle) · Garrett Crochet 15-day-il → 60-Day IL (Lat) · Johan Oviedo 15-day-il → 60-Day IL (Elbow) · Eduardo Rivera day-to-day → 60-Day IL (Back) · Eli White 7-day il → 10-Day IL (Foot) · Ceddanne Rafaela day-to-day → 10-Day IL (Quadriceps) · Masataka Yoshida out → 10-Day IL (Hamstring) · Anthony Seigler day-to-day → 10-Day IL (Wrist) · Willson Contreras 10-day-il → Day To Day (Hand)

CHC

Ben Brown
Neck·Since Jun 23
60-Day IL
Phil Maton
Knee·Since Aug 1
60-Day IL
Riley Martin
Elbow·Since Apr 24
60-Day IL
Cade Horton
Elbow·Since Apr 3
60-Day IL
Porter Hodge
Elbow·Since Mar 24
60-Day IL
Hunter Harvey
Triceps·Since Apr 10
60-Day IL
Shelby Miller
Elbow·Since May 7
60-Day IL
Justin Steele
Elbow·Since May 7
60-Day IL
Trent Thornton
Ankle·Since Sep 11
15-Day IL
Gavin Hollowell
Shoulder·Since Aug 1
15-Day IL
Alex Bregman
Face·Since Sep 20
Day To Day

BOS

Garrett Crochet
Lat·Since Apr 27
60-Day IL
Johan Oviedo
Elbow·Since Apr 1
60-Day IL
Eduardo Rivera
Back·Since Aug 31
60-Day IL
Tanner Houck
Elbow·Since Mar 20
60-Day IL
Kutter Crawford
Forearm·Since May 21
60-Day IL
Zack Kelly
Elbow·Since Jul 20
60-Day IL
Triston Casas
Wrist·Since May 7
60-Day IL
Eli White
Foot·Since Sep 10
10-Day IL
Ceddanne Rafaela
Quadriceps·Since Sep 3
10-Day IL
Masataka Yoshida
Hamstring·Since Aug 15
10-Day IL
Anthony Seigler
Wrist·Since Sep 12
10-Day IL
Curtis Mead
Wrist·Since Aug 1
10-Day IL
Justin Slaten
Elbow·Since Aug 15
15-Day IL
Willson Contreras
Hand·Since Sep 17
Day To Day
Aroldis Chapman
Lat·Since Sep 17
Day To Day

Team Trends

Chicago Cubs

• Chicago Cubs 34-44 ATS at home this season
• Chicago Cubs 47-59 ATS as a favorite this season
• Chicago Cubs 27-20 ATS as an underdog

Season ATS: 75-80 ATS
L10 ATS: 5-5 L10 ATS
L5 ATS: 3-2 L5 ATS
Home ATS: 34-44 home ATS
Road ATS: 41-36 road ATS
As Fav: 47-59 ATS as favorite
As Dog: 27-20 ATS as dog
L10 O/U: 6-3-1 O/U
L10 SU: 6-4

Boston Red Sox

• Failed to cover in 6 of the last 10 games
• Boston Red Sox 33-42 ATS at home this season
• Boston Red Sox 48-61 ATS as a favorite this season
• Boston Red Sox 25-20 ATS as an underdog
• The under has hit in 8 of the last 10

Season ATS: 74-81 ATS
L10 ATS: 4-6 L10 ATS
L5 ATS: 2-3 L5 ATS
Home ATS: 33-42 home ATS
Road ATS: 41-39 road ATS
As Fav: 48-61 ATS as favorite
As Dog: 25-20 ATS as dog
L10 O/U: 2-8 O/U
L10 SU: 4-6

Visit DataStreak for full details

Head-to-Head

BOS 3-2 over CHC

Date	Matchup	Score	Winner
2025-07-20	BOS @ CHC	6–1	BOS
2025-07-19	BOS @ CHC	0–6	CHC
2025-07-18	BOS @ CHC	1–4	CHC
2024-04-28	CHC @ BOS	4–5	BOS
2024-04-27	CHC @ BOS	0–17	BOS

Picks, parlays, injuries, trends, and matchup context powered byDataStreak

The Final Word

Numbers in, narrative out. The plays speak for themselves.

Cubs vs Red Sox FAQ

Where can I find free Cubs vs Red Sox picks for Sunday, September 27, 2026?

Today's algorithmic plays didn't include Cubs vs Red Sox, but our full free MLB picks page covers every matchup that did clear the quality bar.

What's the prediction for Cubs vs Red Sox?

Our prediction is built from team form (records, recent results, win/loss streaks), live moneyline and spread odds across major US books, and DataStreak's algorithmic player-prop research. Every claim on this page is data-backed — no hot takes.

Are these Cubs vs Red Sox best bets really free?

Yes. Every prediction, pick, and parlay on this page is free, no signup, no paywall.

How is The Cover different from Covers, ATS, or pay-for-pick services?

Three things. (1) Free, full stop — every page, every day. (2) Picks are algorithmic with transparent quality bars (8+ game streak, 75%+ hit rate over 20 games), not opinion columns. (3) Modern UX: live odds, push notifications, comments, mobile-first PWA install.