The Chicago Cubs and Boston Red Sox will play two on Friday, Sept. 25, and it's the Cubbies trading as a small road favorite ahead of the 1:05 p.m. ET first pitch of Game 1 at Fenway Park.
My top Cubs vs. Red Sox predictions and MLB picks expect the short turnaround for this early game to lead to a Boston upset.
Who will win Cubs vs Red Sox today: Red Sox moneyline
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This is a simple handicap, and the reason I’d back the Boston Red Sox to 50% is that the Chicago Cubs just clinched a postseason berth last night and traveled for this 1:05 p.m. game in Boston.
The Red Sox lost 1-0 at home Thursday, so I give them a rest and sharpness edge.
Additionally, I’m anticipating that the Cubs will sit a few regulars this afternoon because of the short turnaround and the nor'easter forecast to hit the city.
With the wind howling in and temperatures hovering around 60°F it will be a miserable afternoon for baseball, so I’m looking past the advanced metrics today and betting against the team that splish-splashed champagne all over their clubhouse in a different time zone last night.
COVERS INTEL: The Red Sox bullpen ranks 
Cubs vs Red Sox Over/Under pick: Over 6.5
Even with the weather forecast calling for miserable conditions, the Cubs and Red Sox have enough lineup depth to put runs on the board in hitter-friendly Fenway Park.
Additionally, the Cubs can still host a Wild Card Series, so this isn’t a complete mail-it-in game.
While there isn't confirmation for who will follow Boston opener Alec Gamboa, I’m expecting it to be Jake Bennett, and he’s allowed 12 runs across his past three starts with a 4.91 xERA.
Finally, Chicago righty Clay Holmes (3.84 xERA since joining the Cubs) will give way to a Chicago bullpen sporting a 24th-ranked xERA and 27th-ranked xFIP in September.
- ML/RL picks: 65-38, +32.08 units
- Over/Under picks: 40-34, +3.55 units
Cubs vs Red Sox weather
The forecast calls for an incoming nor'easter bringing miserable conditions with heavy overcast skies, cold temperatures hovering around 60°F, and a stiff 15-25 mph wind blowing straight in from center field.
Cubs vs Red Sox odds
- Moneyline: Cubs 53% | Red Sox 48%
- Run line: Cubs -1.5 (40%) | Red Sox +1.5 (61%)
- Over/Under: Over 6.5 (51%) | Under 6.5 (50%)
Cubs vs Red Sox trend
The Red Sox have won 26 of their last 40 games at home (+3.25 Units / 5% ROI). Find more MLB betting trends for Cubs vs. Red Sox.
How to watch Cubs vs Red Sox and game info
| Location | Fenway Park, Boston, MA |
| Date | Friday, Sept. 25, 2026 |
| First pitch | 1:05 p.m. ET |
| TV | Marquee, NESN |
| Cubs starting pitcher | Clay Holmes (6-8, 3.35 ERA) |
| Red Sox starting pitcher | Alec Gamboa (1-0, 1.16 ERA) |
Cubs vs Red Sox latest injuries
Odds are correct at the time of publishing and are subject to change.
Not intended for use in MA.
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