Confined to their respective leagues for generations with the only concrete history of games between the two storied franchises occurring in the 1906 World Series (in which the White Sox were victorious), Chicago fans only had exhibition games for bragging rights played between the two teams.
Thanks to the introduction of interleague play in 1997 however, a new chapter of history was opened up as a formal rivalry between the two clubs began, with the Cubs and White Sox finally getting the opportunity to play each other in games that count.
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26 years later, the Cubs and Sox have dueled 138 times in the regular season, with the South Siders emerging on top in 73 of those matchups.
With fans on both sides of town anticipating this year's matchup, here's a look back at 13 memorable Crosstown Classic games over the years that show just some of the highs and lows both team's fans have weathered over the years.
6/16/97: Cubs jump out to 6-0 lead, hang on to beat White Sox 8-3 in first-ever regular season Crosstown Classic game
Just a few years removed from fans watching Michael Jordan drive an extra-base hit down the line in an exhibition matchup between the two teams, the long-awaited first regular season game arrived on June 16, 1997 at what was then known as Comiskey Park II.
Chicago White Sox
The Cubs jumped out to an early 6-0 lead off Sox starter Jaime Navarro, partially thanks to two RBI from Brian McRae and Rey Sanchez each, paving the way for an 8-3 North Siders victory.
To honor the historic game, both teams wore throwback uniforms from the beginning of the century. The Cubs donned solid blue throwbacks modeled after 1911 uniforms, while the South Siders wore jerseys similar to their 1906 home set.
Despite the Cubs' win, it was Lyle Mouton of the White Sox who hit the first home run in Crosstown Classic history in this game.
Additionally, four future major league managers started in the game between the two sides (Scott Servais, Ryne Sandberg, Ozzie Guillen and Dave Martinez).
6/13/99: White Sox win 6-4, sweep Cubs at Wrigley Field
1999 marked the first year the two teams would play each other six times, with three games in each team's park. For the White Sox, it was a golden opportunity to seize the first away sweep in Crosstown Classic history, hoping to avenge the Cubs' three-game sweep of the Sox at Wrigley Field in 1998.
Despite Sammy Sosa and Gary Gaetti longballs for the Cubs, the White Sox reigned supreme at Clark and Addison thanks to a dramatic go-ahead two-run shot from shortstop Mike Caruso in the eighth inning.
While both teams finished well below .500 and out of playoff contention in 1999, the sweep-sealing victory did push the White Sox to a game above .500.
6/28/02: White Sox erase 8-0 deficit, Konerko leads comeback in 13-9 win
In a game that initially appeared to be a laugher on the South Side in favor of the Cubs after they jumped out to an 8-0 lead in the third, a classic would soon emerge thanks to an offensive explosion for the White Sox.
Despite Cubs' ace Kerry Wood on the mound and looking in control of the game through the first four innings while only having allowed one run, the Sox began to poke holes in the hard-throwing righty's game.
The following inning, an RBI groundout from Magglio Ordonez and an ensuing two-run shot from Sox icon Paul Konerko suddenly cut the Cubs' lead in half, with plenty more power left to come.
The Sox went on to take the lead in the sixth inning thanks to a rally punctuated by another two-run bomb from Konerko, and didn't look back from there, closing out a 13-9 victory in a riveting comeback.
5/20/06: A.J. Pierzynski, Michael Barrett brawl in Sox shutout victory
Widely regarded to be the rivalry's most memorable moment, it was nothing game-related on this sunny, late-spring day on the South Side that fans remember.
Playing as the defending champions in front of an amped crowd against the then-fledgling Cubs, the difference between the rosters was perhaps as stark as ever.
With the game scoreless in the bottom of the second inning, Sox catcher A.J. Pierzynski moved to tag up from third base on a Brian Anderson flyout.
Upon approaching the plate, Pierzynski collided with Cubs catcher Michael Barrett, successfully scoring before slamming home plate in celebration and bumping into Barrett before trying to head to the dugout.
Barrett visibly took exception to Pierzynski's celebration, and moments later landed a haymaker fans are still talking about.
The benches immediately cleared following the punch, with Barrett, Pierzynski, Anderson and Cubs first baseman John Mabry all being issued ejections.
As if the crowd couldn't be fired up any more, Tadahito Iguchi rocked a grand slam just two batters later, paving the way for a 7-0 White Sox victory.
6/24/07: Cubs shut out Sox 3-0, sweep on South Side for first time
In what perhaps felt like the sweetest revenge after the infamous 2006 trip to the South Side, the Cubs completed a three-game weekend sweep of the Sox with a 3-0 shutout, beginning a stretch of competitive baseball that led to a NL Central title for the Cubs.
Cubs' left-hander Sean Marshall was the star of the show, tossing 6.1 scoreless innings before a bullpen effort from Carlos Marmol, Will Ohman and former South Sider Bob Howry closed out the game.
The Cubs had also taken two of three from the White Sox at Wrigley Field earlier in the season, being the first of the two teams to go 5-1 against the other in a given season.
6/20/08: Aramis Ramirez walks it off to start the weekend
In an unreal season of Chicago baseball in which both teams won their respective divisions and swept each other in their respective ballparks, the Crosstown rivalry was intense throughout 2008, even when the teams were not facing each other.
The season series started on none other than a Friday afternoon in June 2008 at Wrigley Field, with southpaws John Danks and Ted Lilly facing off.
While home runs from A.J. Pierzynski and Jermaine Dye had the Sox ahead most of the game, back-to-back jacks from the dynamic duo of Derrek Lee and Aramis Ramirez quickly tied the game for the Cubs in the bottom of the seventh inning.
It was none other than Ramirez to lead off the ninth inning, who blasted a 1-0 pitch from Scott Linebrink into the left field bleachers for a 4-3 Cubs victory.
6/13/10: Ted Lilly, Gavin Floyd deliver dueling no-hit bids in 1-0 Cubs win
With all Chicago fans riding a high from the Blackhawks' Stanley Cup victory just four days earlier, there was perhaps no better time for the city's two baseball teams to reignite their rivalry at Wrigley Field.
Fans were treated to a pitcher's duel for the ages, with both teams remaining hitless until a two-out double from Alfonso Soriano in the bottom of the seventh inning. Soriano's extra-base knock was followed by a RBI single from Chad Tracy, giving the Cubs the only run they would need.
The White Sox didn't manage a hit off Ted Lilly until the top of the ninth inning, when Juan Pierre led off the inning with a single.
Thanks to two walks after that (one of them being intentional), the White Sox loaded the bases with just one out in the ninth inning, with power hitters Paul Konerko and Carlos Quentin due up.
Cubs' closer Carlos Marmol got Konerko to ground out and Quentin to fly out to short center field to end an atypical 1-0 game.
6/25/10: Carlos Zambrano goes on tirade after rough inning in White Sox shutout win
In perhaps a moment that punctuated the end of an era of competitive Cubs' baseball, former ace Carlos Zambrano was pounced on by the White Sox in the first inning of this series opener, with a Carlos Quentin three-run jack topping off a four-run first for the Sox.
Upon returning the dugout after finishing the inning, Zambrano unleashed a tirade, appearing to chastise Derrek Lee for not making a play on what became a leadoff double for Juan Pierre.
Cubs manager Lou Piniella and pitching coach Larry Rothschild moved to separate Lee from Zambrano, and Zambrano was removed from the game after just one inning.
Zambrano was suspended indefinitely from the team after the tirade, and was temporarily demoted to the bullpen before returning to the rotation late in the season.
As for the game itself, Jake Peavy tossed seven shutout innings while only surrendering three hits in a 6-0 White Sox victory, at the time their tenth win in a row.
5/18/12: Kerry Wood bids farewell at Wrigley Field
A one-time ace and closer who was perhaps remembered more for consistent injury than performance, Kerry Wood and Cubs fans were given what felt like a storybook ending in May 2012.
Though rumors had swirled of Kerry Wood's potential retirement leading up to the game due to his high ERA and continued arm issues, then-Cubs manager Dale Sveum simply said that Wood was available out of the bullpen, not commenting on his future.
Before the game, Wood handed out the lineup card and was seen chasing balls with his son during batting practice.
In a low-scoring affair mostly dominated by strong pitching from starters Jeff Samardzija and Philip Humber, the game took a turn in the top of the eighth inning when Gordon Beckham hit a go-ahead solo shot off Samardzija, giving the White Sox a 3-2 lead.
Samardzija was then replaced by Wood, who came out of the bullpen in what was appearing to be his final outing. Wood faced White Sox outfielder Dayan Viciedo, who he struck out on three pitches.
Then, as Cubs' bench coach Jamie Quirk emerged from the dugout to grab the ball from Wood, it was clear that this was the final showing of one of the most electric pitchers in Cubs' franchise history.
Wood was then greeted by his son as he exited to a roaring ovation from fans of both teams, closing out a phenomenal big league career. He later formally announced his retirement after the game.
The White Sox hung on to defeat the Cubs 3-2.
5/30/13: Travis Wood's grand slam leads Cubs to 8-3 win
The Cubs were always known as a team with a pitching staff that could hit, and that reputation carried over from the era of Carlos Zambrano and Kerry Wood to Travis Wood and Jake Arrieta.
Trailing 2-1 with the bases loaded and nobody out in the bottom of the fourth inning, White Sox starter Jake Peavy challenged Wood at the plate, hoping to snag an easy out.
An easy out, it was not.
Wood's grand slam was half the offense in a 8-3 win over the White Sox, with the Cubs eventually going on to win all four games against the South Siders in 2013.
7/27/16: Aroldis Chapman makes Cubs debut, Báez towering HR leads Cubs to 8-1 win
Shortly after making a blockbuster trade to acquire closer Aroldis Chapman from the New York Yankees, the Cuban Missile couldn't have made his debut in a more electric spot.
Though a low-scoring affair for most of the game with the White Sox in control thanks to a home run from none other than their starting pitcher in Anthony Ranaudo, a home run from eventual MVP Kris Bryant tied the game in the sixth inning.
Then, in the bottom of the seventh, Javy Báez took flight with a towering home run, giving the Cubs a 3-1 lead.
An Addison Russell grand slam in the eighth inning made it a blowout, and Aroldis Chapman entered the game to a raucous crowd to close it out.
6/18/19: Eloy Jiménez hits massive home run in 9th to give White Sox 3-1 win
Formerly a Cubs top prospect who switched sides of town in 2017 when the North Siders moved to acquire Jose Quintana, Eloy Jiménez was looking to exact revenge on his former team at Wrigley Field.
In a quiet 1-1 affair for most of the game, a tense but lively crowd watched nervously as Pedro Strop took the mound in the ninth inning for the Cubs, trying to preserve the deadlock.
After yielding a leadoff single to James McCann, Eloy Jiménez made no mistake on a 1-0 offering:
Alex Colome went on to slam the door for the White Sox in the ninth inning, giving the South Siders a massive 3-1 win in Lakeview.
8/27/21: Bats explode in highest-scoring Crosstown game, Sox win 17-13
In the most recent and perhaps the most wildest entry to the list, the division-leading White Sox and the post-trade deadline Cubs squared off for a slugfest for the ages on the South Side just under two years ago.
The game started out heavily in the Cubs' favor, with Patrick Wisdom smacking a three-run homer before the White Sox could even record an out.
The Cubs went on to score three more times in the first, but that outburst was nothing compared to what the White Sox had in store in the bottom of the third inning.
The White Sox had gotten to Cubs' starter Keegan Thompson, scoring twice before the right-hander could record an out in the inning.
Now a 6-3 game, Adrian Sampson came in to pitch for the Cubs and Yasmani Grandal tied the game with one swing of the bat.
The Sox eventually went on to score eight times in the inning, and opened up a 13-6 lead after the fifth inning.
While the Cubs still had plenty more offense left in them, the White Sox tacked on another four runs and eventually closed out a 17-13 win.
Here's just some of the highlights from the madness:
You can watch this week's Crosstown Classic games on NBC Sports Chicago as the White Sox and the Cubs take each other on from Guaranteed Rate Field this coming Tuesday and Wednesday.