The Memorial Day matchup between the Boston Red Sox and the Milwaukee Brewers on May 26, 2025, at American Family Field pits two middle-of-the-pack teams looking to build momentum as they inch toward the season’s halfway point. The Red Sox, currently 27–28, are striving to find stability in a stacked American League East and enter this game with reasons for optimism thanks to strong recent performance against the spread and encouraging production from both their rotation and heart of the order. Milwaukee, meanwhile, sits at 26–28, just under .500, and is clinging to playoff aspirations in the competitive National League Central, where inconsistency has plagued an otherwise talented roster. Boston is expected to send left-hander Garrett Crochet to the mound, who has quietly emerged as one of the AL’s most effective starters in 2025. With a 4–3 record, 1.98 ERA, and 78 strikeouts in 68.1 innings, Crochet has shown dominant command and a sharp arsenal that could give Milwaukee’s offense fits, especially if he can work ahead in counts. The Red Sox lineup will again be powered by third baseman Rafael Devers, whose 12 home runs and 48 RBIs lead the team and provide the kind of production Boston will need to overcome a Brewers club that’s proven dangerous at home.

On the flip side, Milwaukee counters with right-hander Chad Patrick, who has posted a 3.23 ERA and 45 strikeouts over 53 innings—solid, if not spectacular numbers that suggest he can compete deep into games if supported by good defense and timely hitting. The Brewers’ offense, anchored by veteran Christian Yelich’s 9 home runs, has been productive in stretches but has also shown a tendency to stall, evidenced by their repeated involvement in lower-scoring games. This is further supported by their ATS trend of hitting the game total under in 24 of their last 43 games, suggesting they rely on pitching and defense to win rather than outslugging opponents. Both teams have been hit by injuries, with Boston missing key contributors like Lucas Giolito and Triston Casas, and Milwaukee dealing with absences from Alex Bregman and Nestor Cortes. Despite the setbacks, both squads have managed to remain competitive, and this matchup carries weight for teams hoping to remain within reach of a postseason push. Boston’s ability to consistently cover the run line and perform strongly in the early innings—reflected by their frequent success on the first-five-inning run line—could prove pivotal against a Brewers squad that sometimes starts slow. If the Red Sox can grab an early lead behind Crochet’s power pitching and Devers’ bat, the onus will fall on Milwaukee to respond quickly, a scenario that hasn’t always suited them well this season. Conversely, if Patrick can match Crochet frame for frame and the Brewers can manufacture runs through their contact-heavy approach, this game could hinge on a bullpen battle in the later innings. With two clubs teetering just below .500 and hoping to pivot their seasons, Monday’s contest promises tension, strategy, and potentially October ramifications for whoever manages to seize control.