The Chicago White Sox and Chicago Cubs meet on Sunday, May 18, 2025, at Wrigley Field for the conclusion of their Crosstown Classic series, a rivalry that carries weight far beyond the standings for the city of Chicago. While both teams are on opposite trajectories this season, the matchup still carries high emotional stakes, as the Cubs look to complete the sweep and reinforce their position atop the NL Central, while the White Sox try to salvage a victory in what has been a grim campaign. The Cubs, currently 23–18, have leaned on a blend of veteran consistency and young talent, finding a steady rhythm under new manager Craig Counsell with solid run prevention, effective bullpen usage, and enough offensive pop to win tight games. On Sunday, they will turn to right-hander Colin Rea, who has become a dependable presence in the rotation, giving quality innings and keeping hitters off balance with a varied pitch mix and command of the strike zone. Backing him is a Cubs offense led by Ian Happ and recent acquisition Kyle Tucker, both of whom have contributed power and on-base ability while setting the tone for a lineup that doesn’t rely solely on the long ball but instead manufactures runs with smart base running and clutch hitting. On the other side, the White Sox limp into this finale with a 10–27 record, one of the worst in baseball, and a roster that has struggled across the board—on the mound, at the plate, and in the field.

Sunday’s starter Jonathan Cannon represents a glimmer of hope in a bleak rotation, but the rookie right-hander has had growing pains while adjusting to big league hitters and will need to find a way to limit damage against a Cubs lineup that’s playing with confidence and patience. Offensively, Chicago’s South Side club has gotten some production from Luis Robert Jr. and Miguel Vargas, but too often the lineup lacks traffic on the bases, making it difficult to sustain pressure or mount comebacks. Defensively, the White Sox have been one of the league’s worst units, committing costly errors and failing to make routine plays, which has consistently undermined even their better pitching performances. Their bullpen has been equally unreliable, often giving up inherited runners and struggling with command in high-leverage situations, a trend that has contributed to their inability to close out winnable games. With both teams at opposite ends of the standings and riding contrasting trends, Sunday’s game could be decided early if the Cubs can put up a crooked number in the first few innings and settle into their usual formula of starter-depth followed by a bullpen lockdown. For the White Sox, a win wouldn’t fix the season but could provide a rare bright spot and a morale boost in what has otherwise been a disappointing campaign. For the Cubs, finishing off the sweep at Wrigley would send a strong message to the rest of the NL Central that their early-season success is no fluke, and that they’re ready to contend deep into the summer with a roster that is proving to be both balanced and battle-tested.