5 CrossTown Cup moments that Chicago Cubs fans will never forget

It's a baseball rivalry as iconic as the city that these two teams call home. The Cubs and the White Sox have faced each other twice a year since interleague play began in 1997, with the White Sox holding a 78-74 edge in their all-time series.

The games are always crowded, fun, and hold the potential for chaos, making it a truly awesome Chicago sports rivalry. Here are some of the most unforgettable moments of this historic series that stand the test of time.

5. Michael Jordan's Wrigley Field game - April 7, 1994

Chicago Bulls legend Michael Jordan was able to participate in the Cubs-Sox rivalry before the teams began playing each other during the regular season. In 1994, Jordan was making his brief attempt at being a Major League Baseball player, participating in an exhibition game between the Cubs and the Sox at Wrigley Field.

Jordan was not nearly as good at hitting baseballs as he was at carrying the Bulls to victory on a regular basis, but he was surprisingly able to collect two run-scoring hits in the game. An exhibition game that featured a sold-out crowd full of Chicago fans eager to see if Jordan's unparalleled skills could translate to MLB.

Jordan went on to hit three home runs and post a .202 batting average in 117 games for the Birmingham Barons, the White Sox's Double-A affiliate. After the season was cut short by the 1994 strike, Jordan returned to the Bulls and won them three more NBA championships. But this interesting wrinkle in his career will forever be a part of the Cubs-Sox rivalry.

4. The 1906 World Series

Maybe unforgettable is the wrong word to use for this one since nobody was around for it, but the 1906 World Series is a fascinating case nonetheless. This was the first and only time the Cubs and White Sox have faced each other in the World Series, and the first time that either team made it to the Championship.

The Cubs had won 116 games during the regular season that year, making them automatic favorites. But the White Sox defeated them four games to two to give them their first of three world titles (1917 and 2005). The Cubs would win their first two titles in the next consecutive season in 1907-08 before their infamous 108-year dry spell that was broken in 2016.

It's a matchup that modern fans have pondered and yearned for, with the completeness of the teams' regular-season matchups so potent. One day, this will happen again, and Chicago probably isn't ready for it.

3. Christopher Morel's walk-off home run - August 16, 2023

Two years ago, the White Sox took 2/3 games at Wrigley Field against the Cubs in a three-game series in August. Although the South Siders took more games, the Cubs definitely had the most memorable moment of the weekend.

After trailing the entire game, the Cubs went into the ninth inning down two runs. White Sox reliever Gregory Santos surrendered a double to Cody Bellinger and a walk to Dansby Swanson before Christopher Morel sent a line drive into the right field bleachers for a walk-off three-run homer.

Morel's high energy and enthusiasm for the game of baseball gave Javier Baez a run for his money, and this celebration was no different.

It was one of those storybook moments where a young hitter came through in a huge moment. Since the Cubs weren't able to crack a playoff birth that year, Morel's swing was arguably the best moment of 2023 for the team.

2. Kerry Wood's final game - May 18, 2012

Chicago Cubs Hall of Famer Kerry Wood made his final appearance in MLB during a Friday afternoon tilt with the White Sox. The starting pitcher spent 14 seasons in the big leagues, and 12 of them were with the Cubs.

Wood is forever ensconced in Cubs lore for a variety of reasons, whether it is for his 20-strikeout performance in his fifth appearance in MLB, or his ace-level efforts that helped lead the Cubs to the National League Championship Series in 2003. Wood also stands as one of the best examples of a Cubs homegrown starting pitcher living up to expectations after the team drafted him fourth overall in 1994.

But Wood stands apart from others because of his unyielding loyalty to the organization, which is rare these days. This loyalty became abundantly clear when he returned to the Cubs on a team-friendly deal before the 2011 season. During a press conference after signing his new contract, Wood told fans and media that he had multiple offers from other teams, and that he turned down more money to return to the Cubs because he wanted to raise his family in Chicago.

"It's never been about the money," Wood said. "It's about being home and being here at Wrigley, which is home for me."

Wood was solid in 2011, compiling 51 innings out of Chicago's bullpen with a 3.35 ERA. But prior to the 2012 campaign, Wood's numerous injuries and surgeries over the course of his career caught up to him. The 35-year-old decided to make his retirement on May 18 against the White Sox, where the Cubs allowed him to make one final appearance. After 7.1 innings from starting pitcher Jeff Samardija, Wood took the mound to face one batter in the eighth inning with the Cubs trailing by a run. Naturally, he struck out Sox hitter Dayan Viciedo on three pitches.

Fans and players from both teams gave Wood a thunderous standing ovation as he walked off the mound for the last time and hugged his son on the field.

1. The Barrett Pierzynski brawl - May 20, 2006

It wouldn't be one of the most heated rivalries in baseball without a bit of bad blood. In front of more than 39,000 fans at what was then called U.S. Cellular Field, this rivalry saw perhaps its most bitter moment.

Cubs pitcher Rich Hill had allowed three straight walks to the defending World Series champions in the bottom of the second inning. Hill then induced a flyball to left field from Brian Anderson with White Sox catcher AJ Pierzynski on third base. Pierzynski tagged up and came in to score the game's first run, but not before bowling over Cubs catcher Michael Barrett in the process. It was a legal play from Pierzynski, but Barrett grabbed him before he walked off the field and decked him in the face.

Barret's actions spawned a heated brawl between the Crosstown rivals that forever lives in the memories of both fan bases.