Prior to the inauguration of interleague play in 1997, the White Sox and Cubs played an exhibition game off and on in many incarnations. Those games had some memorable moments. Including a Michael Jordan game winning double down the third base line at Wrigley Field in 1994 and Steve Lyons playing all nine positions.
The rivalry intensified when they began meeting in games that count in ‘97. Many memorable moments have occurred in the 16 years the teams have met. The teams have met 100 times in that span with the White Sox winning 49. Here are the ten most memorable moments since inter league play between the White Sox and Cubs began in 1997T
1998 Brant Brown Walkoff
Brown’s solo home run in the bottom of the 12 inning off Tony Castillo gave the Cubs a 6-5 win.
The Cubs avoided falling behind in the seventh inning after Magglio Ordonez appeared to give the White Sox a 6-5 lead. Wil Cordero had to stop at third on a ground rule double after Ordonez shot in the gap got stuck in the ivy.
1999 Mike Caruso’s 2-Run Eighth inning Home Run Wins it for the White Sox
After a six inning victory in a rain shortened game Friday and a 8-2 win saturday, the White Sox went for their first sweep at a wet Wrigley Field.
Mike Caruso’s two run homerun in the eighth inning put the White Sox ahead 6-4. It provided the winning margin and propelled the South Siders to their first series sweep.
2000 Sosa Home Run off Foulke ties it in the ninth
The White Sox were one out away from ending a two game losing streak against the Cubs. Sosa crushed a Keith Foulke pitch deep into the left field bleachers at Comiskey Park to tie the game at three and send it to extra innings...
2000 Ray Durham Game Winning Double in the 14th inning
In the same game as Sosa’s home run off Foulke, Durham salvaged what could have been a demoralizing loss by driving in Herbert Perry with a double down the left field line in the 14th inning to give the Sox the victory.
2001 Carlos Lee Walk Off Grand Slam
After David Wells was knocked out in the first inning, the White Sox bullpen gave up five hits and no runs in nine innings to set up Lee’s heroics. “El Caballo” hit a two out walk off grand slam in the tenth inning to give the White Sox a 7-3 victory.
2001 Ricky Gutierrez game winning Grand Slam
Gutierrez' eighth inning grand slam off Bob Howry gave the Cubs a 5-1 victory.
2002 White Sox Rally From 8-0 Deficit off Kerry Wood
The Cubs scored eight times in the first three innings to take an 8-0 lead. The White Sox came storming back by scoring ten runs in the middle three innings. Paul Konerko led the charge by going 4-4 with four runs scored, four rbi’s and two home runs.
Kerry Wood gave up six runs in 5.1 innings and Joe Borowski took the loss with two runs allowed in .2 innings.
The White Sox bullpen saved Danny Wright with 6.1 innings and just three hits and one run allowed.
2002 Valentin Walkoff Homerun
After the White Sox scored one each in the sixth, seventh and eighth innings, the Cubs rallied with two in the top of the ninth to tie it. Jose Valentin homered off Antonio Alfonseca with one out and nobody on in the bottom of the ninth to give the White Sox a 4-3 victory.
2006 Michael Barrett-A.J. Pierzynski Fight
The most infamous moments in the 100 game Crosstown Classic series. After Pierzynski scored on a Brian Anderson Sacrifice Fly, Cubs catcher Barrett took exception to Pierzynski slapped home plate after he was called safe. Barrett seemed to think Pierzynski’s exuberance was showboating and he sucker punched Pierzynski on his way back to the dugout.
The White Sox would win up scoring five times total in the second inning. Second Baseman Tadahito Iguchi’s grand slam broke the game open to give the White Sox a 5-0 lead. They would go on to win 7-0.
Barrett wound up being suspended for ten games, Anderson for five and Pierzynski was fined.
2008 First time White Sox and Cubs meet as Division leaders
The White Sox and Cubs first meeting of the 2008 season was significant, because it was the first time the teams were both in first place when they met. When they met June 20th at Wrigley Field, the White Sox had a three game lead over Minnesota and the Cubs a 3.5 game lead over St. Louis.
Home runs by Derek Lee and Aramis Ramirez and again by Ramirez in the ninth inning brought the Cubs back from a 3-1 deficit. They would go on to sweep the three game set at Wrigley. A month later, the White Sox swept the Cubs at U.S. Cellular Field.
2010 Zambrano meltdown
The White Sox hit Carlos Zambrano with a four spot in the first inning, three on a Carlos Quentin homerun.
In the dugout in between innings, Zambrano was seen screaming at Cubs First Baseman Derrek Lee. He thought Lee should have been able to field Juan Pierre’s lead double in the bottom of the first.
Cubs Manager Lou Piniella yanked Zambrano after the first inning and told him to go home. The Cubs demoted Zambrano to the bullpen after the game and he remained there until August.
2010 Sharing the Cup
The most iconic moment of the 100 Crosstown classic game is when the teams kicked off their 2010 meetings on the same day as the Blackhawks Stanley Cup victory parade.
After the parade was held earlier in the day, the Blackhawks brought the cup to Wrigley Field and all three teams took a picture together at the Pitcher mound with the Stanley Cup. This is probably a moment that will never be duplicated.