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White Sox vs. Cubs Betting Odds, Picks & Predictions (Friday, August 21)

White Sox vs. Cubs Betting Odds, Picks & Predictions (Friday, August 21) article feature image

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  • The Chicago White Sox and Chicago Cubs meet at Wrigley Field on Friday night to resume their interleague, crosstown rivalry.
  • The Cubs offense has been solid this season, but the White Sox counter with starting pitcher Dallas Keuchel.
  • Read on for BJ Cunningham's full MLB betting preview for the Crosstown Classic, including odds, picks and predictions for tonight's game.

White Sox vs. Cubs Odds

White Sox Odds -114 [Bet Now]
Cubs Odds -103 [Bet Now]
Over/Under 9.5 (-106/-113) [Bet Now]
First Pitch 8:15 p.m. ET

Odds as of Thursday at 11:30 p.m. ET and via BetRivers. Get up to a $250 deposit match at BetRivers today or see more offers and reviews for the best online sportsbooks.

The battle for the Crosstown Cup resumes Friday night as the White Sox head north to take on the Cubs. The White Sox have rebounded from their slow start and are now only 1.5 games back of Minnesota for first place in the AL Central. The Cubs are firmly holding onto a four-game lead in the NL Central as we approach the halfway point of the MLB season.

Check out our free MLB odds page, which automatically surfaces the best line for every game.

Advanced Stats Glossary

FIP or Fielding Independent Pitching measures what a pitcher’s ERA would look like if the pitcher experienced league-average defense and luck. xFIP  is a regressed version of FIP that adjusts or “normalizes’ the home run component based on park factors.

wRC+ or Weighted Runs Created Plus takes the statistic Runs Created and adjusts that number to account for critical external factors — like ballpark or era. It’s adjusted, so a wRC+ of 100 is league average, and 150 would be 50 percent above league average.

wOBA or Weighted On-Base Average is a catch-all hitting metric with more predictive value than on-base percentage. An average MLB hitter can be expected to post a .320 wOBA. xwOBA is a regressed version of wOBA that accounts for variables like park factors.

BaseRuns is a formula designed to estimate how many runs a team would be expected to score (or allow) given their underlying offensive (or defensive) performance. In other words, BaseRuns is a context-neutral run estimator used to evaluate teams. Major League average for an individual batter per game is 0.50 BaseRuns and a for a pitcher its 0.52 BaseRuns per inning. 

White Sox Projected Lineup

The White Sox have been pretty good offensively through the first half of the season, reporting a .328 wOBA. They also rank eighth in MLB with a 111 wRC+. Tim Anderson has been on fire since he returned from injury, compiling a .466 wOBA and hitting five home runs in 15 games.

The White Sox have also been crushing lefties to the tune of a .389 wOBA, which leads MLB. Cubs projected starting pitcher Jon Lester has been good up to this point of the season, but he may have a difficult time trying to get through this White Sox lineup.

White Sox Projected Starter

Dallas Keuchel, LHP 

Projected & Actual Stats (via Fangraphs)

Pitch Arsenal (via Baseball Savant)

Keuchel has been really good in 2020. He’s posted a 3.94 xFIP, which is better than his preseason projections. His three-pitch arsenal of a sinker, cutter and changeup has been fantastic so far, holding opponents under a .260 wOBA against all of those pitches.

Keuchel is a soft-tossing lefty that is looking to produce ground balls. He has averaged over eight strikeouts per nine innings only once in his career: during his 2015 Cy Young-winning season.

Instead, Kuechel’s success can be correlated with his ground ball rate it. This season, Keuchel has produced a 58.3% ground ball rate, which is slightly lower than his 58.9% career average. Coincidently, his xFIP of 3.94 is also slightly above his career average of 3.53.

The Cubs have been a little below average against lefties so far, reporting a .318 wOBA and 98 wRC+. Of even greater concern, the Cubs also have the seventh-highest ground ball rate against lefties. So, Keuchel’s looming matchup at Wrigley projects favorably on Friday night.

Cubs Projected Lineup

The Cubs offense has been fairly good through Chicago’s first 24 games. The Cubs rank 10th in MLB with a .328 wOBA and a 106 wRC+. Ian Happ has been scorching-hot for the north-siders, accumulating a .456 wOBA, six home runs and 14 RBIs in only 90 plate appearances.

As I mentioned previously, the Cubs have been a little below average against lefties so far this season. So, Keuchel presents a significant challenge for them on Friday.

Cubs Projected Starter

Jon Lester, LHP

Projected & Actual Stats (via Fangraphs)

Pitch Arsenal (via Baseball Savant)

Lester is starting to fall off a cliff as he gets into his late 30s. He’s posted an xFIP over 4.00 in each of his previous two seasons. Through his first four starts this season, he’s been great on paper with a 2.74 ERA. However, his xFIP is 5.36, meaning he’s a house of cards right now.

Lester primarily alternates between his fastball and cutter, and he has fantastic movement on both. However, he’s been getting shelled over the past few years, allowing a wOBA higher than .300 against each of those pitches. He’ll have a tough time against a White Sox lineup that has been crushing lefties so far in 2020.

The White Sox have been fine versus fastballs, but have been struggling versus cutters so far this season (-3.5 weighted cutter runs). So, look for Lester to utilize his cutter a lot on Friday night.


The White Sox bullpen has outplayed their preseason projections, posting a 3.86 xFIP, which ranks third in MLB. On the other side of the coin, the Cubs bullpen has been a major disappointment so far. The Cubs relievers collectively have a xFIP of 4.72, which ranks 22nd in MLB.

The Cubs had the day off on Thursday and Lucas Giolito put in seven solid innings for the Sox, so both bullpens should be fresh and ready to go on Friday.

Projections and Pick

At the time of writing, I don’t see significant value on either side or the total based on my projections. Ideally, I would jump in on the White Sox at +108 or better.

Conversely, if I could find the Cubs at +114 or better, I would pivot to their side. Follow me on the Action Network app to see if I end up making a play on this game.

Pick: White Sox +108 or better; or Cubs +114 or better.

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