​NESN First Pitch: 7:40 p.m. ET. Location: Guaranteed Rate Field, Chicago. The Boston Red Sox aim to extend their winning streak to five games as they face the Chicago White Sox on Wednesday at Guaranteed Rate Field. Boston has been excellent in its latest stretch, piling up an average of seven runs per game during a four-game winning spree and allowing only two earned runs or fewer in all but one contest. Still, questions linger about how long this hot streak can last.
Starting pitcher Jake Bennett will take the mound again, with hopes of exceeding his previous single-season innings record after surpassing his prior total in his most recent start. Bennett carries a 3.10 ERA into his eighth start, having struck out 31 batters over 40.2 innings pitched. Red Sox manager Chad Tracy has kept a near-identical lineup to the series opener, with Masataka Yoshida, Carlos Narváez, and Tsung-Che Cheng entering the lineup in place of Romy González, Connor Wong, and Andruw Monasterio.
For the White Sox, Davis Martin is tasked with steering the team back in the right direction. In a notable development, Braden Montgomery—an acquired centerpiece in the trade that brought Garrett Crochet to Chicago—will make his major-league debut against the team that drafted him, joining Junior Perez in the lineup.
The Red Sox sit with just five games left before the 2026 MLB All-Star break, raising the stakes as they pursue a late-season push. If Boston hopes to position itself for a postseason run, maintaining momentum in these final preseason games will be crucial. This matchup offers a chance to witness a pair of talented clubs jockeying for position as the summer slate dwindles and the All-Star break approaches.