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Crosstown Memory Lane: Best Cubs Moments vs. White Sox

Looking back at some of the best Cubs moments against the White Sox before the 2022 Crosstown Classic gets underway.

Willson Contreras Bobblehead Day Chicago Cubs White Sox Crosstown Classic
Photo: Cubs/Twitter

The Chicago Cubs are set to host the Chicago White Sox in a short two-game series beginning Tuesday. Although both teams have struggled so far to start the season, bragging rights are always on the line when the crosstown rivals clash. Let’s look back at some of the top moments the Cubs have had against the South Siders at Wrigley Field.

May 30, 2013: Travis Wood Smashes Grand Slam

I always love a good “pitcher hits a grand slam” story, especially when it’s against the White Sox. There wasn’t much to be excited about in 2013, as the Cubs were well on their way to another 100-loss season (96, but close enough). Alas, Cubs fans had to find the little things to enjoy that season.

White Sox ace and former Cy Young winner Jake Peavy got the start that afternoon, and let’s just say he didn’t have his “ace” stuff. After already getting recording a hit against Peavy earlier in the game, Cubs starting pitcher Travis Wood smacked a GRAND SLAM in the fourth inning off the former Cy Young Winner. Wood proceeded to throw six innings with six strikeouts to secure the win for the Cubs.

June 20, 2008: Ramirez Plays Hero

2008 was a very exciting season for Chicago Cubs fans. Heading into the franchise’s 100th season since their last World Series championship, fans clamored for 2008 to be “The Year” for the Cubs. To this point, with the Cubs holding a 45-28 record, the North Side faithful had no reason to think otherwise.

Third baseman Aramis Ramirez was an offensive juggernaut for the Cubs. For his career in Chicago, the slugger smashed over 200 home runs and posted a slash line of .297/.359/.892. The 2008 campaign would be his second All-Star season to that point, and this crosstown matchup in June helped carve his way to the Midsummer Classic.

After smacking a game-tying home run in the seventh inning off White Sox reliever Octavio Dotel, Ramirez capped off his heroic performance by hitting a walk-off home run in the bottom of the ninth inning to defeat the South Siders 4-3.

July 12, 2015: Ace Arrieta Dominates

The summer of 2015 was the calm before the storm for Jake “Ace” Arrieta. The All-Star break was right around the corner, and Cubs fans know what happened after the Midsummer Classic. Arrieta would go on to have arguably the greatest second half of a season in the history of baseball, cashing his check that was the National League Cy Young Award.

But before the break, Arrieta faced the White Sox in a crosstown matchup that eventually turned into a preview of what would happen the rest of the season for the righty. For nine innings, Arrieta proceeded to dominate the Sox, striking out nine batters, walking zero, and giving up only two hits. Yea, he did give up one run in the outing, but he made up for it by hitting a home run in the fifth inning to help secure the win and remind the South Siders who the best pitcher in Chicago was in 2015.

June 21, 2008: Edmonds’ Big Inning

Jim Edmonds was nearing the end of his career in 2008, but you wouldn’t have been able to tell by looking at his stats that year. After being traded from the San Diego Padres earlier in the season, the veteran center fielder proceeded to belt 19 home runs with 49 RBIs and a .937 OPS, all in just 85 games for the Cubs.

This mid-summer matchup at Wrigley was just a reminder that sure, maybe Edmonds was a little bit older, but his bat was still a major threat in a lineup that would eventually win the NL Central Division for the second season in a row. White Sox pitchers found out the hard way. In a nine-run fourth inning, Edmonds belted not one, but two home runs. The Cubs went on to beat the Sox 11-7.

May 11, 2018: Willy Shows Out on Bobblehead Day

In 2018, Willson Contreras had already established himself as the Cubs’ starting backstop for the foreseeable future. With the White Sox coming into Wrigley sporting a 9-26 record at the time, and fans receiving a Contreras bobblehead for attending the game, the table was set for the slugging catcher to show out. Contreras went 4-for-5 with two home runs, one being a grand slam, two doubles, and seven RBIs to power an 11-2 Cubs win.

The Chicago Cubs and White Sox will renew their rivalry at 6:40 PM CT on Tuesday night. Left-handed pitcher Drew Smyly will take the ball for the Cubs and face right-handed flamethrower Michael Kopech. Be sure to follow On Tap Sports Net for all your Cubs and White Sox news.

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