The Brewers and Cubs meet Monday for the first time in 2026, opening a three-game series that also serves as their first matchup since Milwaukee beat Chicago three games to two in last October’s Division Series. Brandon Sproat is scheduled to start for the Brewers against Shōta Imanaga for the Cubs.
Milwaukee arrives with the better current form. The Brewers had won eight of nine before losing to the Twins on Sunday, and their 5-1 homestand included a sweep of the Yankees and a series win over the Padres. Since Christian Yelich returned earlier this week after missing about a month with a groin strain, and Andrew Vaughn and Jackson Chourio came back last week from hand injuries, the Brewers have outscored opponents 43-24 and gone 8-2 over a 10-game span. That run has come even though Milwaukee still ranks last in homers.
What has carried the Brewers is the breadth of the roster. Brice Turang has been one of the best all-around second basemen in baseball, Joey Ortiz has given them elite defense at shortstop despite limited offense, and William Contreras with Gary Sánchez gives them a steady backstop pairing. Sal Frelick, Garrett Mitchell and Blake Perkins also make Milwaukee one of the better defensive outfields in the game. The pitching staff has been even more important. The Brewers own a top-five ERA and strong strikeout numbers, with Aaron Ashby and DL Hall anchoring the bullpen, while Abner Uribe and Trevor Megill have flashed electric stuff even if the results have not always been clean.
That depth is why the series feels less like a replay of last October than a new test between two teams that have changed. The opening game will be the first regular-season meeting between the clubs since Aug. 21 of last year, when they finished a five-game set at Wrigley Field. Chicago has played 82 games since then. The numbers are tight enough to show how often this rivalry has run on fine margins: the Brewers lead the all-time series 230-226, the Cubs lead at Wrigley Field 119-110, and in 456 games Chicago has outscored Milwaukee 2,060-2,058. Those figures do not include last year’s Division Series.
The pitching matchups add another layer. On Tuesday, Ben Brown is set to start for the Cubs against Jacob Misiorowski, who has been one of the most overpowering young arms in the sport with a 2.12 ERA, a 2.27 FIP and 80 strikeouts in 51 innings. Wednesday brings Edward Cabrera for Chicago against Kyle Harrison, who has posted a 2.09 ERA, a 2.86 FIP and 48 strikeouts across 38 2/3 innings. Sproat, who starts Monday, has the most difficult line of the three Brewers projected starters with a 5.75 ERA, a 5.74 FIP and 36 strikeouts over 36 innings.
The series is the first real look at how far Milwaukee’s depth can carry it against a familiar opponent that still knows how to make every game feel urgent. The Brewers have spent seven straight full seasons finishing above the Cubs in the Central Division standings, and this matchup begins with the same question that has followed them into October: whether Chicago can close the gap before Milwaukee does it again.
