CHICAGO — The first half of the 2025 Crosstown Classic is set for this weekend at Wrigley Field.
And with a three-game sweep, the Cubs would take the all-time lead over the White Sox heading into the second half of this season’s Crosstown Classic, scheduled for late July at Rate Field.
The White Sox still hold a 74-72 edge in the Crosstown Classic, but the Cubs have closed the gap over the last couple seasons, taking all four games in 2024 to run their Crosstown Classic winning streak to five going back to 2023.
Here’s a look at some of the most memorable moments from the Cubs-White Sox rivalry, going back to before the Crosstown Classic became an annual thing:
Before the Classic
While the Cubs and White Sox are two of MLB’s most historic franchises, their respective paths have often been divergent over the years, despite playing in the same city.
Because the teams are in separate leagues, they didn’t begin playing each other in regular-season competition until 1997, when MLB implemented interleague play. But they’ve played each other regularly since, and these days the Crosstown Classic is an annual part of the regular season.
Prior to that, the North and South Siders squared off many times in exhibition games.
1906 World Series
But only once have they played each other in the World Series. That remains the most significant series the Cubs and White Sox have ever played, almost 120 years later.
In the 1906 Fall Classic, the White Sox — known as the “Hitless Wonders,” because they won the pennant despite having the lowest team batting average in the American League that season — beat the Cubs in six games, securing the title with an 8-3 win in Game 6 at South Side Park III on Oct. 14, 1906.
The “Hitless Wonders” came up with a few big hits at just the right time, too. With the series tied at 2-2, the White Sox scored eight runs each in Games 5 and 6 to finish off the Cubs.
This series happened so long ago that it predated both Wrigley Field and the old Comiskey Park.
Games 1, 3 and 5 were played at West Side Grounds, then home of the Cubs, located on Chicago’s West Side at the corner of South Wolcott Avenue and West Polk Street. Games 2, 4 and 6 were played at South Side Park III, then home of the White Sox, located on the north side of 39th Street (later renamed Pershing Road) between South Wentworth and South Princeton avenues.
City Series
In most years for nearly four decades, from 1903-42, the Cubs and White Sox squared off in a City Series, held concurrently with the World Series.
For an interesting read on the old City Series, check out these pieces by southsidesox.com and the Society for American Baseball Research.
According to the latter, the White Sox won the series 19 times to six for the Cubs. In 161 total City Series games between 1903-42, according to SABR, the White Sox won 95 times and the Cubs 62, with four ties.
Returning from strike
After the 1981 season was interrupted by a players strike, the Cubs and White Sox marked the return of baseball on Aug. 7, playing an exhibition game at Comiskey Park that day and another exhibition game at Wrigley Field the day after.
It was called the Mayor Byrne’s Charity Series.
The first game ended in a 0-0 tie, and the White Sox didn’t score a run at all through the first 14 innings of the two games, noted Paul Sullivan of the Chicago Tribune, one of Chicago’s foremost baseball scribes throughout the years.
Michael Jordan booed?
In April 1994, as Sullivan pointed out, Michael Jordan was booed in Chicago for probably the only time.
During Jordan’s first retirement from the Bulls in 1994, when he was giving baseball a go in the White Sox organization, he was on his way to the minors with Double-A Birmingham. But first, he played with the White Sox in an early April exhibition game against the Cubs at Wrigley Field.
So, being on the South Side team and playing on the North Side, Jordan was booed in Chicago.
He actually had a solid game, finishing with a single, a double and two RBI, along with an error, in a 4-4 tie.
Jordan would never play on an MLB field for a game that counted. But it’s safe to say he returned to the place where he was best, going back to the NBA and leading the Bulls to three more NBA titles, which both Cubs and White Sox fans could cheer for.
This one counts
On June 16, 1997, at Comiskey Park (the new version), Chicago’s two MLB teams met for the first time since the 1906 World Series in a game that counted.
The Cubs won the teams’ first-ever interleague meeting, 8-3, with Brant Brown’s triple to score Brian McRae in the top of the first inning marking the first run in the rivals’ new chapter of history.
The White Sox, however, claimed the three-game series, winning 5-3 and 3-0 in the next two games.
According to the Tribune, WGN’s broadcast of Game 1, which had White Sox announcers Ken “Hawk” Harrelson and Tom Paciorek on the call, was up 136% above the station’s season average for White Sox broadcasts. Game 2, called by Cubs announcers Harry Caray and Steve Stone, was up 74% on WGN’s season average for Cubs broadcasts, according to the Tribune.
Barrett punches Pierzynski
A.J. Pierzynski. Michael Barrett.
Nothing more needs to be said.
But in case anyone needs reminding, it was May 20, 2006, a Saturday afternoon, when the teams met at then-U.S. Cellular Field for the second game of a three-game set.
The White Sox were coming off their World Series title in 2005, plus a 6-1 victory in Game 1 of the series, so the rivalry had gotten especially overheated, with the Cubs cast into the underdog role at the time.
Pierzynski — who else? — provided the spark that ignited an inferno, sliding into home and emphatically touching the plate during the second inning of an eventual 7-0 White Sox victory.
Barrett, the Cubs’ catcher on the play, took exception to Pierzynski’s antics, punching him after the play and starting an all-out brawl.
Later that inning, White Sox infielder Tadahito Iguchi cranked a grand slam.
Indeed, those were better times for the South Siders.
Cubs’ dream season
In 2016, it was the Cubs’ turn to end their World Series drought.
The Crosstown Classic that summer was played out over four consecutive games in late July, the first two at then-U.S. Cellular Field and the last two at Wrigley Field.
The White Sox won their two games at home, but the Cubs rebounded for victories in their two home games. That included a grand slam into the left-center bleachers at Wrigley in the bottom of the eighth by Cubs shortstop Addison Russell in the third game of the series.
Morel’s walk-off
When the teams met in mid-August for the final two games of the 2023 Crosstown Classic at Wrigley Field, the White Sox won the first game, 5-3, and led the second, 3-1, going into the bottom of the ninth.
But Cody Bellinger doubled to lead off the ninth for the Cubs, Dansby Swanson walked, then Christopher Morel belted a 1-2 pitch from Gregory Santos into the bleachers in right-center, giving the Cubs a 4-3 walk-off victory and sending Wrigley into a total frenzy.
That win started a five-game Crosstown Classic winning streak for the Cubs, who won all four games in 2024, that carries into this weekend for the 2025 edition.
Will more memorable moments be added to Crosstown Classic lore? We’ll find out soon enough.