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

The Chicago Cubs face the Boston Red Sox at Tropicana Field in St. Petersburg, Florida, on Sunday, September 27, 2026, in a game rescheduled from Saturday. First pitch is scheduled for 3:05 PM ET with coverage on MLB.TV. Chicago enters at 88-73 overall, while Boston is 87-74. The Cubs sit second in the NL Central, 13.5 games behind Milwaukee, while the Red Sox are third in the AL East, 10.5 games behind Tampa Bay. Boston has already secured the series by sweeping Friday's doubleheader, winning the opener 4-3 and taking the second game 2-0. The Red Sox have therefore won two straight while Chicago enters on a two-game losing streak. At the time of this writing the odds were not released. Be sure to check out our free MLB picks for more MLB predictions throughout the season.

Starting Pitchers

Neither Chicago nor Boston had a probable starting pitcher listed for Sunday's rescheduled game in the information available when this preview was completed. That uncertainty is particularly important after the clubs played a doubleheader Friday and then had Saturday's scheduled game moved to Sunday. Bettors should confirm both starting pitchers before wagering because a late pitching announcement could materially affect both the side and total. With no confirmed matchup available, the handicap has to lean more heavily on the clubs' season-long pitching numbers, offensive profiles and recent performance.

Cubs Look to Salvage the Series Finale

Chicago enters Sunday at 88-73 overall but has dropped four of its last five completed games. The Cubs suffered both ends of Friday's doubleheader in Boston, losing 4-3 and 2-0. They previously edged Miami 2-1 after dropping games against the Marlins by scores of 3-2 and 8-2 in 12 innings. Chicago has scored only nine runs across those five games and has been held to three runs or fewer each time.

The Cubs are batting .251 with 844 runs, 1,385 hits and 218 home runs. Chicago owns a .338 on-base percentage and .427 slugging percentage, giving it a significant season-long offensive advantage over Boston. The pitching staff carries a 4.13 ERA and 1.26 WHIP with 1,253 strikeouts against 497 walks while holding opponents to a .243 batting average.

Chicago's biggest question is whether its offense can rediscover the production represented by those season-long numbers. The Cubs have scored 157 more runs than Boston and hit 56 more home runs, yet Boston held them to only three combined runs across Friday's doubleheader. Chicago has now scored two runs or fewer in four of its last five games. The power remains a major strength, but recent offensive execution has been a concern.

Red Sox Pitching Has Been Outstanding

Boston enters the series finale at 87-74 after taking both ends of Friday's doubleheader. The Red Sox won 4-3 in the first game and followed with a 2-0 shutout. Boston is 3-2 over its last five completed games, with the other victory coming 1-0 against Cleveland. Its two losses were also low-scoring affairs, falling 1-0 and 3-2.

The Red Sox are batting .245 with 687 runs, 1,321 hits and 162 home runs. Boston has a .319 on-base percentage and .398 slugging percentage. The pitching staff has been its stronger unit, producing a 3.52 ERA and 1.23 WHIP with 1,391 strikeouts against 466 walks while limiting opposing hitters to a .240 average.

Run prevention gives Boston its most important advantage Sunday. The Red Sox own a 0.61-run advantage in team ERA and have the better WHIP and opponent batting average. They have allowed only four total runs across their last five games, holding every opponent to three runs or fewer and recording three shutouts during that span. Against a Chicago offense that has simultaneously fallen into a slump, Boston's pitching performance becomes difficult to ignore.

Chicago Cubs vs Boston Red Sox Picks and Prediction

Pick: Boston Red Sox Moneyline

Boston gets the moneyline selection based primarily on the contrast between its recent pitching and Chicago's recent offensive performance. The Red Sox have surrendered only four runs across their last five games, including just three runs over Friday's two games against Chicago. The Cubs have scored only nine runs over their last five and have failed to exceed three runs in any of them. Chicago owns the substantially better season-long offensive numbers, so there is legitimate bounce-back potential, but Boston's 3.52 ERA and 1.23 WHIP provide additional evidence that its recent run prevention is not simply a short-term anomaly. With neither starter confirmed, this is more dependent on the eventual pitching announcements than usual, but Boston is the preferred side based on the available information.

Pick: Under 8.5 or Higher

The under is the stronger betting position if the total is available at 8.5 or higher. Boston's last five games have produced combined totals of two, seven, one, one and five runs, while Chicago's last five have produced two, seven, three, five and ten. The Cubs have scored only nine runs during that span, and Boston has allowed just four. The Red Sox also carry a 3.52 team ERA and 1.23 WHIP into the matchup. The absence of confirmed starters prevents making the total an automatic play at every number, but the recent scoring environment strongly favors another lower-scoring contest. At 8.5 or better, there is enough cushion to back the under.

Final Picks: Boston Red Sox Moneyline and Under 8.5 or Higher

This preview was completed on Saturday, September 26, 2026. Starting pitchers, betting lines and other game information are subject to change before the game begins.