Chicago White Sox vs New York Yankees Prediction and Picks - September 24, 2025
MLB action on Wednesday evening, and we have a Chicago White Sox vs New York Yankees Prediction ready to rock and roll. The White Sox come in with the 2nd-worst record in the league at 58-99. New York currently owns the top Wildcard spot in the American League, but they still have their sights set on the AL East, sitting just one game behind the Blue Jays. Read on to see our White Sox vs Yankees prediction.
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White Sox Closing In On Another 100 Loss Season
The White Sox dropped their 99th game of the season Tuesday night, falling 3–2 to the Yankees in a game that slipped away in the ninth. Rookie Shawn Smith pitched well, striking out eight over five innings and allowing just one run, but the bullpen couldn’t hold a late lead. The offense was limited to seven hits, with Colson Montgomery providing the only spark—a two-run homer in the sixth that briefly gave Chicago the edge. From there, the bats went silent, and the Yankees rallied with two runs in the bottom of the ninth to seal the win.
Jonathan Cannon gets the start Wednesday, looking to avoid the team’s 100th loss. He’s posted a 5.62 ERA across five starts and has struggled to pitch deep into games. Cannon relies on a sinker-heavy mix but has been vulnerable to right-handed power and late-count damage. With a bullpen that ranks near the bottom in ERA and save percentage, the White Sox need length from their starter and early run support to stay competitive. But against a Yankees team fighting for playoff position, that’s a tall order.
Offensively, Chicago is thin. With Luis Robert Jr. and Yoán Moncada sidelined, the lineup lacks punch and plate discipline. Lenyn Sosa leads the team in homers (21) and RBIs (71), but the supporting cast has been inconsistent. Over the past 10 games, the White Sox are hitting just .180 and averaging 2.3 runs per contest. Manager Pedro Grifol continues to rotate young bats like Kyle Teel, Miguel Vargas, and Chase Meidroth, but the production hasn’t followed. With 100 losses looming, Wednesday’s game is less about standings and more about pride—and avoiding another sweep in the Bronx.
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Yanks Move To Within One Game Of The Jays
The Yankees showed once again on Tuesday night why they are such a dangerous team in high-leverage situations. Down 2–1 in the bottom of the ninth, they managed to load the bases and tied the game on a wild pitch before José Caballero blooped a single to bring home Aaron Judge for a walk-off victory. The win not only extended New York’s late-season surge but also officially clinched them a playoff berth, giving fans another reason to celebrate. They have also moved to within 1 game of the Jays in the AL East. Starter Luis Gil turned in a solid outing with six innings of two-run ball, continuing to provide the Yankees with valuable depth in the rotation. While the offense was kept relatively quiet for most of the night, New York capitalized when it mattered most, a hallmark of their season.
On Wednesday, the Yankees will send Max Fried to the mound, and he enters as one of the most reliable pitchers in baseball this year. Fried boasts an 18–5 record with a 2.92 ERA and more than 180 strikeouts, numbers that highlight his dominance and consistency. His ability to command both sides of the plate with a lively fastball and sharp breaking ball makes him a tough assignment for any lineup. Against a White Sox offense that has struggled to score consistently, Fried has the tools to control the game early and set the tone. The Yankees will count on him to provide length, especially after leaning on their bullpen heavily in Tuesday’s dramatic finish.
Offensively, New York continues to lean on the star power of Aaron Judge, who has been at the center of nearly every big rally, but they also benefit from contributions throughout the lineup. Players like Caballero have shown the ability to come through in clutch moments, while younger bats have stepped in effectively when needed. The key for Wednesday will be avoiding wasted scoring chances, as they left multiple runners in scoring position before finally breaking through late on Tuesday. With momentum on their side and Fried toeing the rubber, the Yankees will look to keep the pressure on Chicago from the very start and further cement their postseason readiness.
Chicago White Sox vs New York Yankees Pick
White Sox vs Yankees Moneyline Pick
- NY Yankees -1.5 (5 Units)
The Yankees enter Wednesday’s matchup with all the momentum after Tuesday’s thrilling 3–2 walk-off win, and they now turn to ace Max Fried, who has been one of the most dependable arms in the league this season. With an 18–5 record and a sub-3.00 ERA, Fried gives New York a decisive advantage over White Sox lefty Fraser Ellard, who has yet to notch a win and carries a 4.50 ERA into the start. The pitching disparity alone points toward a game where the Yankees can build an early lead and put Chicago on its heels. Add in the Yankees’ home-field edge and their knack for producing in key moments, and the setup is favorable for them to cover the -1.5 runline.
The White Sox have shown occasional bursts of offense, like Montgomery’s two-run homer on Tuesday, but their inconsistency at the plate and shaky bullpen make it difficult to trust them against an elite contender like New York. If Fried delivers the quality start he’s been known for and the Yankees’ lineup capitalizes on scoring opportunities earlier than they did in the opener, this game has the makings of a multi-run victory. Backing New York at -1.5 provides solid value, especially given how the Yankees’ combination of dominant starting pitching and late-inning resilience matches up against a Chicago team still trying to find answers.
White Sox vs Yankees Over/Under Pick
- Under 8 (5 Units)
The Under 8 looks appealing in this matchup given the quality of Wednesday’s pitching duel. Max Fried has been dominant all year, consistently shutting down opposing lineups, while Chicago’s Fraser Ellard, though inconsistent, has shown flashes of keeping hitters off balance and should be able to limit damage if he avoids big mistakes. The Yankees’ offense has plenty of power, but they were held in check for much of Tuesday’s game and may not need a huge outburst to secure a win behind Fried. Meanwhile, the White Sox offense remains one of the least productive in the league, making it unlikely they’ll generate much against a frontline starter. With both pitchers capable of working into the middle innings and two bullpens ready to handle the late frames, the path to a low-scoring contest is strong, keeping this game Under the 8-run total.
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