Chicago Cubs vs. Chicago White Sox MLB Pick – September 25, 2020

Probable Starters:

    Yu Darvish (7-2, 2.22 ERA) vs. Dylan Cease (5-3, 3.52 ERA)

The Crosstown Cup will close out the season for the Chicago Cubs and Chicago White Sox this weekend. Both teams have clinched a spot in the postseason. There is still business left for the Cubs and White Sox in the regular season, though. Will the Cubs and White Sox go into October as wildcards or divisional winners?

That has yet to be decided. However, it’s looking awfully good for the Cubs. They’re up 2.5 games over the St. Louis Cardinals in the NL Central. That would be some kind of momentum killer if the Cardinals find a way to lose the division.

As of today, the Cubs would be playing the Miami Marlins in the first round. Wrigley Field would be playing host to that three-game series. Meanwhile, the Chicago White Sox would be hosting the New York Yankees at Guaranteed Rate Field.

The White Sox would be a rare commodity if that happened. They’d have homefield, but the Yankees more than likely would be the favorites over the White Sox in the first round. The postseason atmosphere is electric and the White Sox wouldn’t be able to take advantage of that.

The White Sox are coming off a close 5-4 loss against the Cleveland Indians. Dallas Keuchel was sharp across 6 innings, but the bullpen didn’t hold up. Keuchel conceded 4 hits and 1 earned run. The bullpen gave up 4 earned runs, so that was where the White Sox went wrong.

That completed a four-game sweep of the White Sox in that contest. This isn’t a time to be sliding for the White Sox. It can be very hard to flip a switch at the right time in the postseason. Perhaps a meeting against an inter-city rival to conclude the season will get them going in the right direction, though. Head below for our free Chicago Cubs vs. Chicago White Sox pick for September 25, 2020.

Chicago Cubs vs. Chicago White Sox MLB Betting Odds:


  • Cubs -1.5 (+105)
  • White Sox +1.5 (-125)

  • Cubs (-142)
  • White Sox (+131)

  • Over 8.5 (-105)
  • Under 8.5 (-115)

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Chicago Cubs vs. Chicago White Sox Prediction:

Yu Darvish has been a gem for the Cubs this season. He’s often been criticized for not fully living up to expectations in his career, but at least for this shortened 60-game campaign, no one can say anything negative about Darvish. It’s very important for the Cubs that Darvish stays hot in October.

That’s going to be the key to their success in the postseason. Through 12 starts this season, Darvish will post a career-high in his career. His previous career-high was a 2.83 ERA in 2013, so he’ll comfortably break that mark.

Darvish goes into Friday with an ERA of 2.22 and 1.00 WHIP through 69 innings. The only concern for Darvish is that he’s coming off his worst starts of the season. This is a guy that has gone on and off throughout his career, so with his limited sample size up to this point, are we seeing Darvish going to the off position recently? It’s not like he has been terrible by any means, but certainly it doesn’t reflect what he was doing for most of the year.

In his previous three outings, Darvish has posted an ERA of 4.26, 1.32 WHIP, and .309 OBA. He is coming off his worst start of 2020. Darvish was tagged for 9 hits and 4 earned runs in 6 innings of work last week. In 81 at-bats, the White Sox have connected for 5 home runs and 10 RBI against Darvish. After sleepwalking against the Indians, I could see the White Sox returning home to put a little more effort into this final series.

Dylan Cease has felt comfortable pitching at Guaranteed Rate Field in Chicago. He owns an ERA of 1.77 in 20.3 innings at home. During that span, Cease has given up 4 earned runs. In his first meeting against the Cubs this season, he conceded 2 earned runs across 6 innings of work in a 2-1 loss at Wrigley Field. Expect another tight game, with the winner likely decided by a run.


The Bet
Kyle E / Author

Kyle is a veteran of TheSportsGeek and has spent nearly a decade providing accurate sports picks and writeups here. He has been a sports handicapper for 10+ years and started sharing his picks and thoughts in 2011 at TheSportsGeek. His expertise spans across multiple sports, including the NFL, NCAAF, MLB, NHL, and horse racing. Prior to writing for TheSportsGeek, Kyle was a fantasy football expert, who ultimately parlayed it into a successful sports betting career. You can find his picks daily only at TheSportsGeek.