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Home / Predictions / MLB / Chicago White Sox at Chicago Cubs Predictions & Picks – Cubs To Win Crosstown Classic Clash

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Chicago White Sox at Chicago Cubs Predictions & Picks – Cubs To Win Crosstown Classic Clash

Quick Read

  • Chicago White Sox at Chicago Cubs picks for Monday, August 17
  • Game is taking place at Wrigley Field
  • Preview, predictions, stats & form
Leigh Copson
Written by Leigh Copson
Sports Editor25+ Years Experience, US & Combat Sports Specialist
Updated: Aug 17, 2026
mlb

(Getty Images)

Chicago White Sox at Chicago Cubs Predictions & Picks

The Cubs are tipped to return to winning ways in the Crosstown Classic.

They have been solid at home despite those defeats at the end of last week, and they can get after Sox starter Luis Castillo who, despite a strong showing last time out, has given up a bunch of hits and runs in recent outings.

  • Chicago Cubs are 9-4 in their last 13 games
  • White Sox starter Luis Castillo is 4-9 with a 4.96 ERA this season
  • Chicago Cubs are 7-3 in the previous 10 meetings
  • The Over cashed in the 3 previous meetings this season

Head To Head

  • Chicago Cubs lead the all-time series 81-80
  • Chicago White Sox won 9-8 when the two teams last met on May 17

Chicago White Sox Form

Chicago White Sox enter this series on an improved run of form, having responded to a four-game losing skid by winning six of their previous eight games.

DateOppositionW/LScore
Aug-06 at Boston Red Sox L 11-12 W/O
Aug-07 vs Cleveland Guardians L 2-8
Aug-08 vs Cleveland Guardians W 6-3
Aug-09 vs Cleveland Guardians W 5-3
Aug-11 vs Cincinnati Reds L 4-5
Aug-12 vs Cincinnati Reds W 5-0
Aug-13 vs Cincinnati Reds L 8-9
Aug-14 at Detroit Tigers W 9-5
Aug-15 at Detroit Tigers W 4-3
Aug-16 at Detroit Tigers W 7-5

Chicago Cubs Form

Chicago Cubs go into this matchup having won nine of their previous 13 games, but having suffered three defeats in their last four.

DateOppositionW/LScore
Aug-06 vs Toronto Blue Jays W 3-2 W/O
Aug-07 at Kansas City Royals W 6-4
Aug-08 at Kansas City Royals L 3-6
Aug-09 at Kansas City Royals W 10-2
Aug-11 at Washington Nationals W 8-6
Aug-12 at Washington Nationals W 12-6
Aug-13 at Washington Nationals L 0-7
Aug-14 vs St Louis Cardinals W 3-0
Aug-15 vs St Louis Cardinals L 4-8
Aug-16 vs St Louis Cardinals L 4-11

Starting Pitchers

PlayerTeamRecordERAStrikeoutsInnings
Luis Castillo Chicago White Sox 4-9 4.96 101 110.2
Shota Imanaga Chicago Cubs 8-9 3.74 130 137.1
Leigh Copson
Leigh Copson

Sports Editor25+ Years Experience, US & Combat Sports Specialist

During his career he has covered some of the biggest sporting events on the planet, including the Super Bowl, the Champions League Final and the World Cup Final. He has also covered almost every major boxing match and UFC fight card during this time.. His specialist sports are American Football, Basketball, Ice Hockey, Boxing, Mixed Martial Arts and Football.


Follow more of Leigh's work on Muckrack.

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