Chicago Cubs vs Boston Red Sox Picks and Prediction for Sunday, September 27, 2026

The Chicago Cubs and Boston Red Sox meet Sunday at Tropicana Field, with the opening pitch scheduled for 3:05 PM ET and the game televised on MLB.TV. This is the final regular-season game for both clubs. The game was moved to Tropicana Field due to a storm that is expected to hit Boston on Sunday. Chicago is 88-73, second in the NL Central, and has clinched a wild-card spot. The Cubs lost twice to Boston on Friday, 4-3 and 2-0. Boston is 87-74, third in the AL East, and has also clinched a wild-card spot. The Red Sox have won two straight entering the finale. Let’s break down the matchup with our free MLB picks. 

Chicago Cubs Trying to Finish the Regular Season With a Win

Chicago has dropped four of its last five games, with the lone victory coming 2-1 against Miami on Thursday. Pete Crow-Armstrong has produced a huge season, batting .280 with 45 home runs, 107 RBI, 119 runs and 41 stolen bases. Seiya Suzuki is hitting .268 with 26 homers, 86 RBI and a .365 on-base percentage, while Alex Bregman has 26 home runs, 89 RBI and a .350 on-base percentage. Nico Hoerner has added a .262 average, 163 hits and 23 stolen bases.

The Cubs are batting .251 with 841 runs, 218 home runs, a .339 on-base percentage and .429 slugging percentage. Chicago ranks sixth in MLB batting and 17th in pitching with a 4.15 ERA, 1.26 WHIP and .243 opponent average. Cubs pitchers have allowed 230 home runs while recording 1,239 strikeouts. Chicago has been particularly reliable defensively, ranking first in MLB with only 60 errors and a .990 fielding percentage. The Cubs have a 42-38 road record this season.

Injuries: Phil Maton (out), Hunter Harvey (out), Tyler Austin (out), Trent Thornton (out).

Boston Red Sox Building Off Consecutive Wins

Boston took both Friday games against Chicago, winning 4-3 before recording a 2-0 victory. Ceddanne Rafaela leads the Red Sox with a .282 average and 152 hits, adding 16 home runs, 70 RBI and 17 stolen bases. Willson Contreras has been Boston’s main power source with 27 home runs and 81 RBI, while batting .276, with a .387 on-base percentage and .518 slugging percentage. Wilyer Abreu has contributed 24 homers, 76 RBI, and 38 doubles across 155 games.

The Red Sox are batting .246 with 681 runs, 162 home runs, a .319 on-base percentage and .399 slugging percentage. Boston ranks 15th in MLB batting, but its pitching staff ranks third with a 3.55 ERA, 1.23 WHIP and .241 opponent average. Red Sox pitchers have recorded 1,378 strikeouts while allowing 151 home runs. Boston has also recorded 17 shutouts this season. Defensively, the Red Sox rank tied for 13th with 81 errors and a .986 fielding percentage.

Injuries: Tanner Houck (out), Johan Oviedo (out), Anthony Seigler (out), Masataka Yoshida (out), Zack Kelly (out).

Pitching Matchup

Chicago Cubs - Undecided

Chicago had not yet announced its starting pitcher at the time this preview was written.

Boston Red Sox - Undecided

Boston had not yet announced its starting pitcher at the time this preview was written.

Chicago Cubs vs Boston Red Sox Game Pick

• Boston Red Sox

Boston is the pick after winning both Friday meetings against Chicago while allowing only three total runs. The Red Sox also have the clear season advantage on the mound, ranking third in MLB with a 3.55 ERA and 1.23 WHIP compared with Chicago’s 4.15 ERA and 1.26 WHIP. Boston has allowed 605 runs this season, while Chicago has surrendered 701. The Cubs have dropped four of their last five, and Boston’s pitching numbers make the Red Sox the play in Sunday’s regular-season finale.

Chicago Cubs vs Boston Red Sox Over/Under Pick

• Under

Under is the pick with Boston’s pitching staff allowing only 605 runs this season while posting a 3.55 ERA and 1.23 WHIP. The Red Sox have held opponents to a .241 average and recorded 17 shutouts, including Friday’s 2-0 victory over Chicago. Four of Boston’s last five games have finished with five combined runs or fewer. Chicago has also scored only nine runs across its last five contests, with three of those games finishing with three combined runs or fewer.