MLB Rivalries: Chicago Cubs vs Chicago White Sox 

Michael Barrett and AJ Pierzynski fighting in 2006.

In this edition of MLB Rivalries, we’re looking at another cross-city rivalry; The Crosstown Classic between the Chicago Cubs and the Chicago White Sox.

This time, we’re really opening a can of worms too, as Cubs fan and Bat Flips and Nerds team contributor Sean Guest and his younger brother Gary, a White Sox fan, will look at what the rivalry means to each team and to the city.

Sean and Gary Guest at the 2019 London Series games (image credit: Sean Guest)

Just how important is it to not only be the Pride of the Second City, but to have bragging rights in the Guest family?

First, given their familial ties, let’s start with how Gary and Sean each became fans of rival teams.

Gary Guest

Despite watching MLB on Channel 5 in the UK when I was a kid, I didn’t adopt a team until 2009 after I paid a brief visit to Chicago.

Ozzie Guillen’s White Sox team were at home to the Angels and Lou Piniella’s Cubs were on the road in Cincinnati. So, I headed to what was then called US Cellular Field (now Guaranteed Rate Field) and saw the White Sox beat the Angels 5-4 with a walk-off win in the bottom of the ninth from Scott Podsednik with two outs.

I saw home runs from Gordon Beckham and Carlos Quentin, and got hooked on the Sox and baseball from that night onwards, regularly tuning in to games back home in the UK.

Sean Guest 

Growing up, I had a minor interest in baseball. I enjoyed watching Ken Griffey Jr. in particular, but preferred basketball.

However, when my brother came back from the US in 2009 and told me he’d become a fan of the White Sox, I thought it would be fun if I were to start following one of their rivals.

Assuming baseball rivalries worked like football rivalries do, I picked the Cubs, and found myself immediately drawn to Wrigley Field, their iconic uniforms and the ‘loveable loser’ mentality of the fanbase. My interest was fleeting for the first couple of years, but as the Theo Epstein-led rebuild gathered steam, so did my fandom.

I owe my love of the Cubs entirely to my brother though and appreciate that, if he hadn’t gone to that Sox game in 2009, I wouldn’t have started following the team, I probably wouldn’t have started writing for Bat Flips & Nerds and I probably wouldn’t have met all the great people that make up the UK fanbase. 

Chicago Cubs

The Cubs-White Sox rivalry dates back to the year 1900, when Charles Comiskey moved his Saint Paul Saints minor league franchise to Chicago. The Cubs bristled at the prospect of the local competition, even though they played in the National League and their new rivals were one of the founding members of the newly-established American League.

It took six years for the two teams to actually play one another competitively but their first meeting was a significant one, as they went head-to-head in the 1906 World Series – the first ever to feature two teams from the same city. Despite being heavily favoured, the Cubs ended up losing in six games, handing the White Sox their first ever World Series title, not to mention local bragging rights.

The 1906 World Series-winning Chicago White Sox (Image credit: public domain)

Three years prior, baseball had sanctioned a best-of-seven postseason City Series that took place whenever the two teams failed to make the playoffs. Between 1903 and 1942, the series took place 25 times in total, with the White Sox winning 18 and the Cubs winning six.

In 1985, the two teams introduced the annual ‘Windy City Classic’ charity game, which ran until 1995 and saw the White Sox go 10–0–2. Two years later, inter-league play was introduced, giving the local rivals an opportunity to play one another competitively each season. To spice things up further, in 2010 they introduced the ‘Crosstown Cup’, a largely meaningless trophy that goes to the team that wins each year’s regular season series.

Numerically speaking, the rivalry hasn’t been particularly favourable for the Cubs. While both teams have won three World Series apiece, the Sox have won more league pennants (17-6), division titles (8-6), and playoff appearances (21-11). Head-to-head, the two teams have played a total of 148 regular season and postseason games against one another, with the Cubs recording an inferior overall 70-78 (47.3%) record.

Between 2015 and 2020 – the Cubs window of contention, which, of course, saw them win the World Series – they just about edged the White Sox, going 17-13 over their rivals during that span.

After spending the subsequent two years on the wrong side of the series, they bounced back this season, taking three of the four games the two teams played against one another.

The Cubs got the better of the White Sox in 2023, wininng three of their four meetings

Although they weren’t ultimately able to register another playoff appearance, the Cubs do very much appear to be in the ascendancy once again while the White Sox’s window of contention has blown shut after just a couple of seasons of limited success.

What that means for this long-standing rivalry and the local bragging rights that go along with it is anyone’s guess though.

Sean Guest is Bat Flips & Nerds’ Chicago Cubs contributor, and can be found on Twitter @SW_Guest.

Chicago White Sox

Stellar seasons have been rare of late for the Chicago White Sox, but 2005 was the exception. It was one of the most successful in franchise history and saw the team achieve not only the best record in the American League, but the second-best in all of baseball (99-63).

Thanks to a powerful offense led by Sox legend Paul Konerko and a solid pitching staff charged by Mark Buehrle, the Sox went on to win the World Series that year, defeating the Houston Astros in five games to end a drought that dated back to 1917.

Since then, times have been hard for the ballclub. Fans have been forced to ensure several rebuilds that have produced just three playoff appearances while having to watch on as the neighbouring Cubs ended their own World Series drought in 2016.

As a lifelong football fan, I’ve experienced many intense rivalries in person before and I was unsure what to expect when I went to Chicago. But that between the Cubs and the Sox is tangible. Riding the Red Line train from the station at Sox-35th back to downtown Chicago after a Sox win can be a noisy affair, particularly if the Cubs lost that day, with Sox fans chanting in celebration about their rival’s defeat. I’m sure the same goes for those travelling back from Wrigley Field when the Cubs are victorious, and the Sox have been defeated (which in recent times has been all too regular!)

Notably, in 2006, the year after the White Sox won the World Series, Cubs catcher Michael Barrett fuelled the rivalry in a heated exchange with White Sox catcher A.J Pierzynski when they collided at home plate with Pierzynski trying to score. Barrett appeared to block the plate to prevent Pierzynski from scoring, resulting in a fierce charge from A.J, knocking Barrett to the ground and a celebratory ‘slap’ of home plate. Barrett returned to his feet and right hooked the White Sox catcher, resulting in the benches clearing and chaos ensuing.  

Michael Barrett and A.J Pierzynski had a shall we say ‘full and frank exchange of views’ in 2006…

It’s moments like these that remind onlookers how intense this rivalry can be as fans strive for bragging rights over their crosstown neighbours. White Sox fans may have enjoyed a wry smile when the Cubs came so close to making this year’s postseason, but having finished with a 61-101 record themselves that signalled the end of the ‘Change the Game’ era, they will be keen to see what new general manager Perdro Grifol can do to turn the ship around and get their team competing again.

Gary Guest is a Chicago White Sox fan and the younger brother of Chicago Cubs contributor Sean Guest.


No matter how they came to their respective fandoms, both Gary and Sean have picked teams that each have a rich and, at times, chequered history (the 1919 World Series scandal, for example).

More importantly, following their respective teams also enriches both of their lives; Gary continues to enjoy watching baseball here in the UK, while Sean initially wanting to wind his brother up a little by supporting the White Sox’s North Side rivals has led to a love for and frequent visits to the Second City, as well as the wonderful articles that he contributes to this website.

I’m just not sure I’d want to be around on those occasions when the Cubs and White Sox are playing each other, and the Guest family gather for Sunday dinner!

Brett Walker is the Oakland Athletics contributor for Bat Flips & Nerds, and can be found on Twitter @BrettChatsSport.

Featured image – Phil Valesquez/Chicago Tribune

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