Chicago Cubs vs Boston Red Sox Prediction 9/25/2026 Today’s MLB Picks

The Chicago Cubs and the Boston Red Sox meet Friday in MLB action from Fenway Park. 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 Clay Holmes for game one of the doubleheader and Holmes is 6-8 with a 3.25 ERA and 75 strikeouts this season. David Peterson will get the start in game two and is 9-8 with a 4.96 ERA and 131 strikeouts this season. Boston will send out Alec Gamboa for game one and Gamboa is 1-0 with a 1.16 ERA and 22 strikeouts this season. Brayan Bello will start game two and is 6-7 with a 4.49 ERA and 90 strikeouts this season.

Chicago Cubs Recap

The Chicago Cubs come into this game looking to add on to their 2-1 win over Miami last time out to sit at 88-71 this season. 

Cubs Snap Two-Game Slide

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 bounce back from a 1-0 loss at the hands of the Cleveland Guardians last time out to sit at 85-74 this season.

Red Sox Lose 4 Of Last 5

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 25, 2026: Game 1

• Probable Starting Pitcher: Alec Gamboa      Record this season: 1-0      ERA: 1.16
• Home Record: 0-0
• Last 5 against Cubs: –

Why the Boston Red Sox will win

• The Red Sox have won each of their last five games as underdogs against NL opponents.
• The Cubs have lost four of their last five games as favorites following a win.
• The Red Sox have covered the run line each of their last 11 Friday games against teams that held a winning record.
• The Cubs have failed to cover the run line in nine of their last 10 games following a home win.
• The Cubs have lost the first inning in three of their last four games at Fenway Park.
• The Cubs have trailed after 3 innings in five of their last six games at Fenway Park.
• The Cubs have trailed after 5 innings in each of their last four day games against AL East opponents.

• Probable Starting Pitcher: Clay Holmes      Record this season: 6-8      ERA: 3.25
• Road Record: 3-5
• Last 5 against Red Sox: 2-1

Why the Chicago Cubs will win

• The Cubs have won 14 of their last 16 road games against AL opponents following a home win.
• The Red Sox have lost four of their last five games.
• The Cubs have covered the run line in eight of their last nine road games against AL opponents.
• The Red Sox have failed to cover the run line in 11 of their last 12 games following a loss.
• The Cubs have led after 3 innings in each of their last four games against opponents that held a winning record.
• The Cubs have led after 5 innings in each of their last four games against opponents that held a winning record.

Total Runs Facts

• Each of the Red Sox’s last seven games have gone UNDER the total runs line.
• Each of the Cubs’ last four road 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 Cubs’ last six road games against AL opponents.
• There has been no run scored during the first inning in nine of the Red Sox’s last 10 home games.

Boston Red Sox Player Prop Facts

• Ceddanne Rafaela has hit at least one home run in each of the Red Sox’s last three games as underdogs against NL opponents.
• Trevor Story has recorded at least one hit in each of his last 16 home appearances against NL Central opponents that held a winning record.

Chicago Cubs Player Prop Facts

• Ian Happ has hit a home run in four of the Cubs’ last five road games against AL opponents.
• Clay Holmes has recorded five or more strikeouts in four of his last five appearances with his team as a road favorite against AL opponents.
• Alex Bregman has recorded at least one hit in each of his last 14 appearances against the Red Sox.
• Pete Crow-Armstrong ranks T1st in the league in Home Runs (45) this season.

Matchup/League Facts

• The Red Sox rank T1st in the league for home runs allowed this season (151).
• The Red Sox rank 2nd in the league for doubles this season (281).
• The Cubs rank 1st in the league for runs scored this season (841).
• The Cubs rank 1st in the league for RBIs this season (795).

The Chicago Cubs @ Boston Red Sox Betting Trends: September 25, 2026: Game 2

• Probable Starting Pitcher: Brayan Bello      Record this season: 6-7      ERA: 4.49
• Home Record: 3-2
• Last 5 against Cubs: 1-1

• Probable Starting Pitcher: David Peterson      Record this season: 9-8      ERA: 4.96
• Road Record: 6-3
• Last 5 against Red Sox: 2-1

Chicago Cubs Player Prop Facts

• Pete Crow-Armstrong ranks T1st in the league in Home Runs (45) this season.

Chicago Cubs vs. Boston Red Sox Prediction

I’m on the under in both games. The Cubs have struggled against lefties so that could be a problem in game one and Brayan Bello has really found some game since rejoining the Red Sox rotation as of late. On the flipside, Holmes and Peterson are two solid options for the Cubs and could be competing for innings work in the postseason so I’ll back the under in both games and I think we at least get a split.

Chris Ruffolo's Pick: UNDER