Cubs vs. Red Sox Dunkel MLB Picks, Predictions and Prop Bets - Sept. 27

The Boston Red Sox have a 2-0 series lead and aim to sweep the Chicago Cubs on Sunday at Tropicana Field, at 3:05 p.m. ET. The Cubs are 88-73 this season, second in the NL Central. The Red Sox are 87-74, third in the AL East. Neither team has named a starter.

Despite playing away from home the Cubs are at -124 to win, compared to the Red Sox at +102. The game's over/under is set at 7.5.

Cubs vs. Red Sox Odds, Game Time

• Game day: Sunday, September 27, 2026
• Game time: 3:05 p.m. ET
• Location: St. Petersburg, Florida
• Stadium: Tropicana Field
• Favorite: Cubs (-124)
• Underdog: Red Sox (+102)
• Over/under: 7.5

How to Watch Cubs vs. Red Sox

• TV Channel: NESN and MARQ
• Live Stream: Fubo (Watch for free)

Bet now on FanDuel Sportsbook!

Cubs vs. Red Sox: Betting the Moneyline

• The Cubs have compiled a 63-51 record in games they were listed as the moneyline favorite (winning 55.3% of those games).
• Boston has been victorious in 26, or 53.1%, of the 49 contests it has been chosen as underdogs in this season.
• Chicago has a record of 52-42 in games when oddsmakers favor them by at least -124 on the moneyline.
• The Red Sox have a mark of 14-20 in contests where bookmakers favor them by +102 or worse on the moneyline.
• The implied moneyline probablility for this matchup gives the Cubs a 55.4% chance to win.
• The moneyline set for this matchup implies the Red Sox have a 49.5% chance of coming away with a victory in the contest.

Cubs vs. Red Sox: Betting the Spread & Total

• The Cubs have played in 161 games with set over/under, and have combined with opponents to go over the total 89 times (89-67-5).
• Boston's games have gone over the total in 70 of its 161 chances.
• The Cubs have covered 46% of their games this season, going 74-87-0 ATS.
• In 161 games with a line this season, the Red Sox have a mark of 77-84-0 against the spread.