Chicago Cubs vs Boston Red Sox Picks and Prediction for Sunday September 27 2026
Cubs Preview
Historic Fenway Park will play host to the regular season finale between the Chicago Cubs and the Boston Red Sox. The Cubs (88-73) have clinched a playoff spot and will likely travel to San Diego for the National League Wild Card series. In the first game of Friday’s doubleheader, Chicago batters went 2-for-11 with runners in scoring position and left eight men on base during a 4-3 road loss against Boston. Get in on all the action with our free MLB picks.
Chicago skipper Craig Counsell has not named a starting pitcher for this contest. The Cubs rank in the middle of the majors with a 4.13 ERA and a 1.26 WHIP. Chicago starters have logged 52 quality starts. The Cubs rank 13th with a 3.95 bullpen ERA and use a close by committee approach.
Red Sox Preview
The Boston Red Sox have not won a playoff series since winning the 2018 World Series and will face New York in the American League Wild Card series. In the second game of Friday’s doubleheader, Wilyer Abreu delivered a two-run double in the eighth inning to lift Boston to a 2-0 home victory. Jedixson fired five shutout innings in relief and fanned five batters to earn the win for the Red Sox (87-74), who moved to 41-39 at home.
Boston manager Chad Tracy has not announced a starting pitcher for the regular season finale. The Red Sox rank third in the majors with a 3.52 ERA and a 1.23 WHIP. Boston starters have notched an impressive 64 quality starts. The Red Sox rank fourth in bullpen ERA and are anchored by veteran closer Aroldis Chapman (1.92 ERA).
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Cubs vs Red Sox Pick
Boston 1B William Contreras is dealing with a hand injury and his availability for Game One of the wild card series is uncertain. Through 161 games, Chicago ranks 1st in OPS and 1st in runs scored. For the season, Boston ranks 17th in OPS and 22nd in runs scored. The Red Sox are locked into their spot, while the Cubs need a win or a Philadelphia loss in their final two games to clinch the fifth seed. Take Chicago to win on the road. Final Score Prediction, Chicago Cubs win 6-2.
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