Yankees vs. White Sox Prediction, Odds, Probable Pitchers and Prop Bets for Friday, Aug. 29

Iain MacMillan | Aug 29, 2025

The White Sox are home underdogs against the Yankees on Friday night. / Matt Marton-Imagn Images

The New York Yankees took care of the Chicago White Sox on Thursday night, winning their fifth straight game.

They'll do their best to keep beating the White Sox this weekend as they try to catch the Toronto Blue Jays atop the AL East. Can the White Sox pull off the upset on Friday night? It might be more likely than you think.

Yankees vs. White Sox Odds, Run Line, and Total

Odds via Caesars Sportsbook

Run Line

• Yankees -1.5 (-140)
• White Sox +1.5 (+118)

Moneyline

• Yankees -235
• White Sox +192

Total

• Over 9 (-105)
• Under 9 (-115)

Yankees vs. White Sox Probable Pitchers

• New York: Carlos Rodon, LHP (14-7, 3.24 ERA)
• Chicago: Yoendrys Gomez, RHP (3-1, 4.73 ERA)

Yankees vs. White Sox How to Watch

• Date: Friday, August 29
• Time: 7:40 p.m. ET
• Venue: Rate Field
• How to Watch (TV): YES, CHSN
• Yankees Record: 74-60
• White Sox Record: 48-86

Yankees vs. White Sox Best MLB Prop Bet

• Andrew Benintendi OVER 0.5 Hits (-140) via BetMGM

The time to bet on Andrew Benintendi is when the White Sox are facing a left-handed pitcher. His batting average this season improves from .227 against righties to .267 against lefties. Chicago takes on a left-handed starter tonight in Carlos Rodon, so let's bet Benintendi to record at least one hit at -140 odds.

Yankees vs. White Sox Prediction and Pick

In today's edition of Walk-Off Wagers, I broke down why I'm betting on the White Sox to pull off the upset:

If you want to place a bet on a huge underdog tonight, consider the White Sox at +192 against the Yankees. Their offense has been better than you'd think since the All-Star Break, especially against lefties. In that time frame, they have an .806 OPS and a wRC+ of 122 against left-handed pitchers.

That will prove to be important against Carlos Rodon, who has a 3.62 ERA and a 1.255 WHIP on the road this season.

That's enough to warrant a bet at +192 on the underdog White Sox at home.

Pick: White Sox +192 via Caesars

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