The best White Sox moments against the Cubs in recent memory

With the 2025 Crosstown Cup getting started this weekend, here's a look at the best recent Chicago White Sox moments that have come against the rival Cubs.
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The Chicago White Sox and Chicago Cubs renew their crosstown rivalry this weekend at Wrigley Field.

With the current sad state of the White Sox, the rivalry is more about bragging rights and city culture than it is the actual on-field product these day.

Sure, it would be nice to see the White Sox beat the Cubs and keep the North Siders slumping, but the Cubs have their sights on playing playoff baseball in October while Sox fans are hoping to finish with the best MLB Draft Lottery odds.

But even when both Chicago teams are not in contention, Sox-Cubs means something to Chicagoans. It has always been North Side against South Side. American League baseball versus National League baseball. Big brother versus little brother. You pick your side, and every year, one fanbase gets the bragging rights.

Instead of immediately celebrating the new pope hailing from Chicago, everyone wanted to know where his loyaly lied: Was a Cubs or Sox fan? WGN had to send a reporter out to Pope Leo XIV's brother's house to confirm he was a Sox fan.

This year especially, this rivalry means more to the fans than it does in the standings. Over the years, the Crosstown Classic has produced some entertaining games and iconic moments.

Here are the best White Sox moments against the Cubs over the past 25 years...

June 18, 2019 - Eloy Jimenez and the "Thanks, Cubs" home run

Eloy Jimenez might be the most disappointing player in White Sox history, but he did have a tendency to haunt his former team. The Cubs traded Jimenez along with Dylan Cease to the White Sox for Jose Quintana back in 2017.

Jimenez went on to hit some massive home runs at Wrigley in a White Sox uniform. None bigger or more famous than his a game-winning, two-run home run in the ninth inning on June 18, 2019.

Jason Benetti's call of "Thanks Cubs!" after the homer is something White Sox fans will never forget. In that moment, it felt like the Cubs had gifted the Sox a perennial MVP candidate.

September 21, 2018 - The White Sox tally 19 hits and hand the Cubs a loss they could not afford to take.

The White Sox were tanking and lost 100 games in 2018, but on September 21st, they played like the best team in baseball by pounding out 19 hits to win 10-4 over the Cubs at home.

White Sox outfielder Ryan LaMarre went 3-for-3 with 3 RBIs that night.

It was a big loss for the Cubs, who were leading the NL Central with the Milwaukee Brewers hot on their heels late in the season. The Cubs and Brewers ended the season tied at the top of the standings and Milwaukee went to win the tie-breaking game at Wrigley.

Had the Sox not crushed all those hits, the Cubs would have completed the sweep and would have won their third-straight NL Central Division title.

May 20, 2006 - Michael Barrett brawls with A.J. Pierzynski as the Sox crush the Cubs 7-0

This will always be the moment when the rivalry was at its best. The 2000s were when the teams made six combined playoff appearances and the White Sox won the whole thing in 2005. The Cubs were five outs away from going to the World Series in 2003.

However, in 2006, the Cubs were coming apart while the Sox were still basking in the glow of winning the World Series.

Tempers flared after Cubs catcher Michael Barrett took exception to A.J. Pierzynski slapping home plate after a collision at the plate.

Pierzynski was also one of the most disliked players around the league, but one of the most beloved by White Sox fans. A brawl ensued, and it further cemented Pierzynski as a hero on the South Side.

The White Sox marketing department used that event as part of a slogan, "Punch A.J.," to get him voted in as the final AL All-Star representative.

June 28, 2002 - White Sox rally back from being down 8-0 thanks to Paul Konerko's big day

Paul Konerko took a pitch from Kerry Wood off his face in the second inning, but shurgged it off and went 4-for-4 with two home runs as the Sox rallied to win 13-9.

The Cubs jumped out to an 8-0 lead in the third inning. Then the Sox started to slowly come back.

Konerko's first home run was a two-run shot to cut the Cubs' lead down to 8-4 in the fifth. He came up again in the sixth and put the Sox ahead with another two-run blast.

June 8, 2001 - Carlos Lee's walk-off grand slam

Tied 3-3 with the bases loaded and two outs in the bottom of the 10th inning, Carlos Lee stepped up to the plate to face Cubs' reliever Courtney Duncan.

"El Caballo" crushed a 0-1 pitch to left, setting off the fireworks and causing the South Side faithful to go into a frenzy in the stands.

Lee had a knack for going yard against the Cubs, he had 39 bombs against them in his career, none more memorable than this one.