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Chicago White Sox at Chicago Cubs Betting Tips – Cubs To Win Crosstown Classic Clash

leigh-copson
Editor
Last updated: Mon 17 Aug 2026 09:40
In the highly anticipated Crosstown Classic, the Chicago Cubs aim to bounce back and secure their 10th win in 14 games against the White Sox. While the White Sox have won six of their last eight games, Cubs are tipped to capitalize on their solid home performance and exploit the inconsistency of Sox starter Luis Castillo (4-9, 4.96 ERA). Head-to-head, the Cubs have taken seven of the past ten matchups. The recommendation is to back the Cubs for a home victory.
Leigh Copson 1 hour ago
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  • Cubs have won 9 of last 13 games and 7 of last 10 vs White Sox
  • White Sox in better recent form but Cubs favoured at home
  • Sox starter Luis Castillo has struggled; backing Cubs for the win
(Getty Images)

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.

Key Numbers – Can Cubs Make It 10 Wins In 14 Games?

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

Cubs Lead All-Time Head-To-Head; Sox Won Last Meeting

  • 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 – Last 10 Games

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 – Last 10 Games

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

Verdict

The White Sox are the team in better form, but we are backing the Cubs to take this.

The hosts have done a decent job at home this season, and they should enjoy plenty of offensive success against a starter who has been hittable this season.

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leigh-copson
Leigh Copson

Sports Editor • 25+ 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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