As the series resumes Tuesday night at Wrigley Field, here are some of the best and worst moments from someone who has covered all 118 games:
Who else? Pierzynski's two-out, three-run homer off Ryan Dempster in the ninth inning of a 2006 game at Wrigley Field gave the Sox a stunning 8-6 win. According to the Elias Sports Bureau, it was only the fourth time in the previous 20 years that the Cubs lost a home game in which they led with two outs and no one on base in the top of the ninth. Cubs fans, who had booed Pierzynski the entire game, littered the field after the homer.
"Am I going to be Bartman from now on?" Pierzynski said. "But that's the way it is. Fans have to have a hero and an enemy, and I guess I'm the enemy."
Longest rain delay
Wrigley Field, 1999
A 3½-hour rain delay at Wrigley led most Cubs fans to either go home or to the bars, leaving the ballpark to Sox fans. Shortstop Mike Caruso rewarded them with his first home run of the season, a two-run, eighth-inning shot off Rick Aguilera that gave the Sox a 6-4 win, ending a day that lasted 6 hours, 15 minutes, including the delay.
"We played guts out, 1 through 9," Sox first baseman Frank Thomas said. "Everybody did a part. Everybody had a moment the last three days. This was a special series and a special weekend."
Angry Cubs fans who exited during the delay tried to get back in, and the police were called. Many bought $8 standing-room tickets just to get back inside.
Joe Maddon, 2016
When controversial closer Aroldis Chapman arrived in a trade from the Yankees in time for the City Series, Maddon was asked if anyone would care if Chapman was a good person if he wound up saving Game 7 of the World Series.
"Was Ty Cobb wonderful?" Maddon said. "I don't know. To judge him as a good or bad person, that's your right. But I know there (have been) times when I have been less than perfect. I think we all could agree we've all been less than perfect."
Chapman blew the save in Game 7 of the World Series when he gave up a game-tying home run to Rajai Davis but helped the Cubs win their first title since 1908.
Jerry Reinsdorf, 1997
White Sox Chairman Jerry Reinsdorf was so pleased with the first interleague matchup in 1997 he immediately called for realignment. "We should go the next step and shuffle the leagues and the divisions," Reinsdorf said. "The Cubs, White Sox, Milwaukee and St. Louis should be in the same division. But it won't happen."
Maybe it will happen someday, but thankfully not yet.
Funniest profane T-shirt
After the Sox's World Series win in 2005, their fans wore T-shirts featuring a cartoon of a world championship Sox ring on the middle finger of a one-fingered salute. "This One's For You," it read.
Cubs fans, naturally, had one of their own made after 2016.
Best dugout confrontation
Lou Piniella vs. Milton Bradley, 2009
"This young man has put a lot of pressure on himself," he said. "He needs to relax and let his ability flow. Look, personally, I like Milton. He's just trying too hard and then he's fighting it. That just compounds the problem over and over and over again. And I had had enough."
Bradley was suspended from the team later in the season.
Ozzie Guillen, 2011
Before Cody Parkey's double-doink, perhaps the most famous 21st century kick in Chicago was executed by Sox manager Ozzie Guillen. After an argument at the plate in a game at U.S. Cellular Field, Guillen booted Cubs catcher Geovany Soto's mask as Soto stood by and laughed.
"Twenty years ago I might have broken my toe," Guillen said. "But they make the mask so light now I didn't feel anything."
Greatest trash talker
The White Sox shortstop homered and mocked Sammy Sosa's patented gesture of kissing his fingers and tapping his heart. "I'm not going to apologize because I don't think I did anything to offend anyone," Valentin said. "Sammy has no problem with it, so I won't say I'm sorry." It was classic Valentin.
Most emotional moment
Kerry Wood's last game, 2012
The Sox won, 4-2, at Wrigley, but the game was remembered as the last in the 14-year career of Cubs pitcher Kerry Wood, who struck out Dayan Viciedo and walked off the field to a standing ovation. His son, Justin, ran out of the dugout for an embrace.
"We don't all get to choose when; we don't all get to have a say in it," Wood said. "But I was fortunate enough to play this game a long time and play in a wonderful city in front of the best fans in baseball. It was just time."
Cubs blow 8-run lead, 2002
The Cubs led 8-0 before the Sox rallied for a stunning 13-9 win at what was then called new Comiskey Park. Wood hit Paul Konerko in the helmet with a breaking ball in the fourth inning before Konerko hit a two-run homer off Wood in the fifth and a two-run shot off Joe Borowski in the sixth to give the Sox a 10-8 lead.
"After those first couple of innings I didn't see any swagger," Sox manager Jerry Manuel said of the Cubs. It was the biggest blown lead for the Cubs since 1976, when Mike Schmidt hit four home runs to help the Phillies escape a 12-1 deficit.
Piniella ripped into Sox broadcaster Steve Stone after Stone had criticized Piniella's handling of young outfielder Tyler Colvin. "Steve Stone? He has enough problems doing what he does with the White Sox," Piniella said. "What job has he had in baseball besides talking on television or radio? What has he done?
"Why isn't he a farm director and bring some kids around? Why isn't he a general manager (or) put the uniform on and be a pitching coach? Why hasn't he been a field manager? There are 30 teams out there that could use a guy's expertise like that. I'm tired of some of these guys, I really am." Piniella then went on to include TV/radio personality David Kaplan in his criticism, which came before the game even started.
Michael Barrett vs. A.J. Pierzynski, 2006
No contest. When Barrett punched Pierzynski after their collision at the plate, it ignited the City Series like nothing else. It's the punch that keeps on giving, and a moment that will be talked about as long as the series is played.