Crosstown Classic. Redline Rivalry. Crosstown Cup.

North vs. South.

Cubs vs. Sox.

While New York and LA may have two teams as well, Chicago’s rivalry is unlike any other.

Dating back to the early 1900s when Charles Comiskey moved his team from Saint Paul to Chicago, there have been two teams fighting for supremacy.

Between 1903 and 1942, the two teams, when neither won the league pennant, played a best-of-seven post-season series. Starting in 1985, the two teams played the “Windy City Classic”, a charity game alternating between the two teams’ home stadiums. In 1994, Michael Jordan even got involved as the right fielder during the game, as he was part of the White Sox farm system during his time away from basketball. 

Since 1997, when inter-league play began, the Sox and Cubs have played each other at least three times a year. The Sox are currently leading the all-time regular season series 70-64.

At both Wrigley Field, and at Guaranteed Rate/US Cellular/Comiskey Park, the Sox hold a record of 35-32. 

Barrett vs. Pierzynski

Not everything about this rivalry is remembered just by the scores. There have been a few notable moments between the two franchises. The most notable came in May 2006.

Many fans will remember the moment from the instant it happened. With AJ Pierzynski standing on third base, a deep fly ball was sent to the outfield by Brian Anderson. Pierzynski tagged up and attempted to score on the throw to the plate.

Cubs catcher Michael Barrett attempted to tag Pierzynski, who collided with the catcher. Barrett dropped the ball, Pierzynski slapped home plate, and as he walked back to the dugout was blocked by the Cubs catcher.

He punched him in the face. That punch cost Barrett 10 games, and caused a benches clearing brawl. The Sox would go on to win the game 7-0, but that moment would live on.

Playing for Both Sides

The two teams have shared more than memories. They have shared 284 different players and a few play-by-play personalities. 

Ron Santo, Sammy Sosa, Phil Cavarretta, Don Kessinger, and Juan Pierre all played for both franchises at some point in their careers, and they aren’t even the tip of the iceberg. 

More recent players like Jose Quintana, Eloy Jimenez, Craig Kimbrel and Nick Madrigal have impacted both teams in their stints with the two teams. 

2022 Meetings

This season both teams are off to below average starts. When they meet, next Tuesday at Wrigley, it’s possible both teams will be under .500 and looking to turn around the season with some crosstown momentum. 

The projected starters are Mark Leiter Jr. vs. Michael Kopech in game 1, and Drew Smyly facing off with Lucas Giolito in game 2. 

This short two game series could be ugly for the Cubs, if they aren’t able to get any offensive production. Their bullpen has looked strong so far, so a lead after the 6th inning would be very helpful for a team looking for it’s identity. 

I honestly see a split between the teams, with the Sox taking the first game, and Cubs taking game two.


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