Chicago Cubs vs Boston Red Sox Prediction 9/27/2026 Today’s MLB Picks

The Chicago Cubs and the Boston Red Sox meet Sunday in MLB action from Tropicana Field. We will look at this from a betting perspective and determine the best bets for this game. Here’s a Chicago Cubs vs. Boston Red Sox prediction.

Starting Pitching Matchup

The Chicago Cubs will send out Shota Imanaga for the start here and Imanaga is 11-10 with a 3.74 ERA and 171 strikeouts this season. The Boston Red Sox did not have a starting pitcher announced at the time that this article was posted.

Chicago Cubs Recap

The Chicago Cubs come into this game looking to rebound from a 2-0 loss at the hands of the Red Sox on Friday to sit at 88-73 this season.

Cubs Trying To End Regular Season On High Note

Pete Crow-Armstrong leads the Cubs across the board with a team-high 173 hits, 45 home runs, and 107 RBIs alongside 31 doubles and 8 triples so far this season. Nico Hoerner has logged 163 hits with 29 doubles, a triple, 8 home runs, and 72 RBIs, while Alex Bregman has contributed 157 hits with 32 doubles, 2 triples, 26 home runs, and 89 RBIs on the year. Michael Busch has added 141 hits with 27 doubles, 2 triples, 20 home runs, and 77 RBIs, and Ian Happ has recorded 119 hits with 28 doubles, 3 triples, 24 home runs, and 68 RBIs. Carson Kelly has chipped in 98 hits with 15 doubles, 10 home runs, and 58 RBIs, while Dansby Swanson has registered 91 hits with 16 doubles, 3 triples, 19 home runs, and 69 RBIs for Chicago up to this point in the season.

Boston Red Sox Recap

The Boston Red Sox come into this game looking to add on to their win over the Cubs to improve to 87-74 on the year.

Red Sox Looking To Stay Hot Entering Postseason

Ceddanne Rafaela leads the Red Sox with a team-high 152 hits while adding 32 doubles, 3 triples, 16 home runs, and 70 RBIs so far this season. Wilyer Abreu has added 147 hits with 37 doubles, 4 triples, 24 home runs, and 74 RBIs, while Willson Contreras leads Boston with a team-high 27 home runs and 81 RBIs alongside 123 hits, 21 doubles, and 3 triples on the year. Caleb Durbin has contributed 125 hits with 25 doubles, a triple, 13 home runs, and 64 RBIs, while Jarren Duran has logged 113 hits with 15 doubles, 5 triples, 20 home runs, and 69 RBIs for the Red Sox up to this point in the season.

The Chicago Cubs @ Boston Red Sox Betting Trends: September 27, 2026

• Probable Starting Pitcher: Patrick Sandoval      Record this season: 1-7      ERA: 5.07
• Home Record: 1-2
• Last 5 against Cubs: –

Why the Boston Red Sox will win

• The Red Sox have won each of their last seven games as underdogs against NL opponents.
• The Cubs have lost each of their last six day games against AL opponents that held a winning record.
• The Red Sox have covered the run line in each of their last seven games as underdogs against NL opponents.
• The Cubs have failed to cover the run line in nine of their last 10 day games against AL opponents that held a winning record.
• The Cubs have trailed after 5 innings in four of their last five day games against AL East opponents.

• Probable Starting Pitcher: Matthew Boyd      Record this season: 10-5      ERA: 3.91
• Road Record: 4-2
• Last 5 against Red Sox: 2-2

Why the Chicago Cubs will win

• The Red Sox have lost six of their last seven games at Tropicana Field.
• The Cubs have won 13 of their last 16 day games against AL East opponents following a loss.
• The Cubs have covered the run line in eight of their last nine games against AL opponents following a loss.
• The Red Sox have failed to cover the run line in four of their last five day games against NL opponents following a win.
• The Red Sox have trailed after 5 innings in 11 of their last 14 games at Tropicana Field against opponents that held a winning record.
• The Cubs have led after 3 innings in five of their last six games against opponents that held a winning record.
• The Cubs have won the first inning in three of their last four games as favorites against the Red Sox.

Total Runs Facts

• Eight of the Red Sox’s last nine games have gone UNDER the total runs line.
• Four of the Cubs’ last five games against AL opponents have gone OVER the total runs line.
• There has been at least one run scored in the first inning in each of the Red Sox’s last six day games against NL opponents.
• There has been at least one run scored in the first inning in 10 of the Cubs’ last 12 games against AL opponents.

Boston Red Sox Player Prop Facts

• Patrick Sandoval has recorded four or more strikeouts in 14 of his last 15 appearances with his team as an underdog.
• Ceddanne Rafaela has recorded at least one hit in each of his last 12 appearances with the Red Sox as underdogs against NL opponents.

Chicago Cubs Player Prop Facts

• Nico Hoerner has recorded at least one hit in each of the Cubs’ last 10 Sunday games against opponents that held a winning record.
• Matthew Boyd has recorded five or more strikeouts in each of his last six appearances in day games against AL teams that held a winning record.
• Matthew Boyd has recorded a win in each of his last five appearances with the Cubs as favorites against AL opponents.
• Pete Crow-Armstrong ranks T1st in the league in Home Runs (45) this season.

Matchup/League Facts

• The Red Sox rank 1st in the league for home runs allowed this season (151).
• The Red Sox rank 2nd in the league for doubles this season (285).
• The Cubs rank 1st in the league for runs scored this season (844).
• The Cubs rank 1st in the league for RBIs this season (798).

Chicago Cubs vs. Boston Red Sox Prediction

I’m on the under here. I just think that in a nothing game there’s not a lot of motivation here between two teams that clearly have their sights set on their respective playoff paths ahead. Add in the fact that this game has been relocated to Tampa Bay andI think it just creates a sense of going through the motions and the under is where it’s at here.

Chris Ruffolo's Pick: Under 7.5