Sid Ranks Em’ All: Sid’s Top 5 White Sox Moments Against The Cubs

Sidney Brown has quite the encyclopedic brain for all sports. In “Sid Ranks Em’ All” you get to read his unique take on the best and worst of sports with specific lists spanning all playing fields.

By Sidney Brown (@sidkid80)

Round 2 of the 2019 edition of the Crosstown Showdown will take place tonight on the South Side between Chicago’s Cubs and White Sox. There have been countless moments that have inflamed this storied rivalry since it became a regular season occurrence via the inception of Inter League play in 1997. 

As a devoted Sox fan, I’m proud to say that my team leads the all-time series 61-59 entering this weekend. With many memories stacked for a lifetime, here’s my top five moments from this ever-heated and interesting city rivalry.

5) June 11-13, 1999: Sox Sweep Cubs at Wrigley

After being swept the year before at the Friendly Confines, the Sox were looking for revenge. Game 1 saw young stars Magglio Ordonez and Greg Norton each tally 2 RBI each for a 5-3 win. 

The next day saw the resurgence of veteran Frank Thomas with a long ball and 2 RBI to his credit. Ordonez added two more RBI en route to a 8-2 victory. Game 3 saw the Men in Black respond once more courtesy of a Mike Caruso home run and RBI’s from Greg Norton, Carlos Lee, Ray Durham and Ordonez for the 6-4 win, sweeping away the North Siders and winning the season series 4-2.

4) June 28 & 29th, 2002: Paulie Has a Day

The first match-up on the South Side from this year was essentially a coming out party for Paul Konerko, who belted 2 home runs and 4 RBI, while Magglio Ordonez contributed with 3 RBI in a 13-9 slug fest. The next day featured Frank Thomas, who drove in three runs to help edge out the Cubs 5-4. 

Konerko’s hot streak for the month of June helped clinch his first ever all-star appearance that Summer.

3) May 20th & 21st, 2005: Teamwork Makes Dream Work

The Sox were on a magic carpet ride to start the 2005 season, running up win after win, but one of their first real tests came against their city rivals. 

Game 1 featured a dominating performance from pitcher Freddie Garcia while Joe Crede and Jermaine Dye provided home runs for a 5-1 win. Game 2 saw the Sox win in comeback fashion, scoring 4 runs in the 8th inning, including another dinger from Jermaine Dye and 2 RBI each from Paul Konerko and Carl Everett for the 5-3 win on enemy turf.

2) July 1, 2006: AJ Beats Back Upset Effort

Coming off a World Series title from the year before, the Sox had a lot to prove on the field while the championship gave South Siders the upper hand in bragging rights over their North side counterparts. 

In this back and forth affair, the Sox had home runs from Jim Thome, Paul Konerko and Joe Crede. With the game tied at 6-6 in the 9th inning, AJ Pierzynski delivered a game-winning, two-run homer off closer Ryan Dempster for an 8-6 dramatic victory. 

Pain was felt on the other side when Cubs radio analyst Ron Santo slammed his headset and walked out the booth as Pierzynski’s shot landed on Sheffield Avenue.

1) June 18, 2019: Eloy’s Revenge

With a World Series title in hand for the Cubs and a turning of the corner in the rebuild for the Sox, the Crosstown Showdown has become meaningful for both sides of town. 

Kyle Schwarber delivered his 16th home run of the year to give the home team an early 1-0 lead. As the game unfolded with all the tenseness of a playoff encounter, another memorable chapter to the city rivalry was closed when former Cub prospect Eloy Jimenez belted a two-run shot onto Waveland Avenue off Pedro Strop, giving the Sox a 3-1 win.

The dramatic finish will have Cubs fans wondering for a long time what happiness they could’ve had if Eloy was allowed to make the majors in a Cubs uniform.

Sidney Brown is WARR Media's resident Chicago sports historian 
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