Cubs Vs. White Sox Betting Preview: Lines, Analysis Of 2020 Crosstown Cup

Written By Joe Boozell on August 21, 2020 - Last Updated on September 16, 2020

The White Sox will travel 8 miles north this weekend to take on the Chicago Cubs at Wrigley Field in a three-game series.

Here’s everything sports bettors in Illinois need to know about the 2020 Crosstown Cup.

Friday odds, props

Here are the Friday (Aug. 21) lines at DraftKings and BetRivers sportsbooks, which both use the same Kambi odds.

As of now, DK and BR are the only two Illinois sports betting options in the Land of Lincoln:

  • White Sox (-113 ML) vs. Cubs (-104 ML)
  • Over 9.5 runs (-107); under 9.5 runs (-114)
  • Dallas Keuchel over 3.5 strikeouts (+100); under 3.5 strikeouts (-130)
  • Jon Lester over 4.5 strikeouts (-118); under 4.5 strikeouts (-109)

Schedule,  pitching matchups

  • Game 1: Friday, 7:15 p.m. CST (Dallas Keuchel vs. Jon Lester)
  • Game 2: Saturday, 7:15 p.m. CST (TBA vs. Kyle Hendricks)
  • Game 3: Sunday, 1:20 p.m. CST (Dylan Cease vs. Yu Darvish)

If fans were in the stands, this would be the most anticipated Cubs versus White Sox series in a decade.

That’s mostly because the White Sox are, you know, good this year. The Pale Hose have won five straight and carry a 15-11 record into Wrigley despite enduring numerous injuries.

Meanwhile, the Cubs have cooled off a bit since their searing start. Though, at 16-8, they are the clear No. 2 team in the National League behind the Dodgers.

The White Sox are favored on Friday, but don’t be surprised if they are underdogs on Saturday and Sunday due to the pitching matchups.

Keuchel has been as advertised thus far. He’s 3-2 with a 3.07 ERA to go with a sturdy 3.55 FIP. He’s been Rick Renteria‘s most reliable starter this season.

While Lester has actually been better from a statistical standpoint, the 36-year-old lefty’s stuff leaves much to be desired at this stage.

Will Lopez start for the Sox on Saturday?

Reynaldo Lopez was the Sox’s No. 3 starter coming into the season.

He lasted all of 0.2 innings in his first start before heading to the IL with shoulder soreness.

Saturday would appear to be Gio Gonzalez‘s turn in the rotation, but Renteria has yet to announce a starter. Reports indicate that Lopez could return that day.

It won’t matter much from a betting perspective, as Hendricks has the clear edge in the matchup. He has a sub-1 WHIP in 2020.

On Sunday, Cease gets a chance to face the team that traded him (along with Eloy Jimenez) for Jose Quintana. Cease has been much better in his second year than he was as a rookie, boasting a 3.16 ERA.

But beware, potential White Sox bettors: He’s been the beneficiary of good luck. Cease has a 6.14 FIP, which is worse than his 2019 FIP despite posting a 5.79 ERA last season. It’s going to be a tough spot for him on Sunday against a deep, motivated Cubs offense.

Speaking of luck

The Cubs have had some this year. Their expected record based on run differential is 14-10, two games worse than their actual mark. The White Sox, on the other hand, are playing to their expected record.

The Cubs have the second-best record in the NL by several games. However, the Rockies, Padres and Braves are all just two runs or fewer behind them in run differential.

Both teams have nagging injuries

Luis Robert and Yasmani Grandal missed the White Sox’s Thursday drubbing of the Tigers they are considered day-to-day, and one (or both) could return for the Cubs series. On the other side, Kris Bryant will return “Friday, at the earliest,” after receiving a wrist injection.

The Cubs would certainly welcome Bryant back, but it would seem unwise to replace Ian Happ in the leadoff spot. Happ has a 1.109 OPS on the year, compared to Bryant’s icy .594 mark. If Bryant returns this weekend, expect to see him lower on the lineup card than usual.

For the White Sox, weird as it may seem, Illinois bettors should be more concerned with Robert’s health than Grandal’s.

That’s partial because they arguably have the best backup catcher in the league in James McCann. Robert is also a two-way terror, carrying a .847 OPS into the weekend to go with a 1.2 WAR (T-17th in MLB). He leads the Sox in that category, with apologies to Tim Anderson, who likely would if not for missing time with a groin injury.

It’s not going to look the same as a typical Cubs-White Sox series (the Michael BarrettA.J. Pierzynski brawl feels more like it). But both teams enter this series with serious playoff aspirations, a welcomed change in Chicago compared to the last decade.

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Joe Boozell

Joe Boozell has also been a college sports writer for since 2015. His work has also appeared in Bleacher Report, and Growing up, Boozell squared off against both Anthony Davis and Frank Kaminsky in the Chicagoland basketball scene ... you can imagine how that went.

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