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The Biggest MLB Rivalries of All Time: 2023 Edition

biggest MLB rivalries

What are the biggest MLB rivalries of all time? This is a league that is the oldest major professional sports league in the world which was created in 1876.

Biggest MLB Rivalries 

As one of the most popular sports in America and national sport, Major League Baseball has the oldest and most historical rivalries. Even the newer derbies have created a deep divide between fans. Let’s take a look at the five biggest MLB rivalries. 

5. Chicago White Sox vs. Chicago Cubs

The Chicago Cubs are a member of the National League, and the Chicago White Sox are a part of the American League. Although the two teams have a historical rivalry, inter-league play only began in 1997. 

Since the 1906 World Series between the Cubs and White Sox, which stopped the city, the rivalry has been limited to the City Series and Windy City Classic charity game because of the different leagues the teams were in. 

The White Sox and Cubs have played each other at least six times a year since 2010, and the best team takes home the Crosstown Cup trophy. 

What makes the White Sox-Cubs game one of the biggest MLB rivalries is that the Cubs are based on the North Side of Chicago and the White Sox are based on the South Side. The rivalry is just one of a number of reasons why Chicago is one of the best sports cities in America.

One of the most iconic moments in the White Sox-Cubs rivalry was in 2006 when Cubs catcher Michael Barrett punched White Sox catcher A. J. Pierzynski after the two collided, with both benches clearing as a result. 

White Sox fans are also mocked for having “Little brother syndrome”, as they’ve historically been overshadowed by the Cubs. The White Sox received little fanfare when winning the 2005 World Series, compared to when the Cubs won it in 2016.

Even Michael Jordan has appeared in the White Sox-Cubs game, with the former Chicago Bulls superstar playing in an exhibition match for the White Sox thanks to his connection with the White Sox minor-league affiliate team the Birmingham Barons.

4. Milwaukee Brewers vs. Chicago Cubs

The Brewers-Cubs rivalry is relatively new with the first match played in 1997, but it’s fast become one of the biggest MLB rivalries. The MLB rivalry has been built on the biggest NFL rivalry of all time between the Chicago Bears and Green Bay Packers.  

The distance between the home fields of the Brewers and Cubs are only 83 miles apart (134 km). Brewers fans get irritated when Cubs fans refer to American Family Field (formerly known as Miller Park) as Wrigley North, in reference to Chicago’s home ballpark Wrigley Field. 

Because it’s often easier and cheaper to travel and watch the Cubs play in Wisconsin than it is to watch a home game at Wrigley Field, Brewers home games almost feel as if they’re away games, as Chicago fans make the trip in big numbers in support of the Cubs.  

It’s such an issue that the Brewers launched the “Take Back Miller Park” campaign which was launched in 2006. In return, a large contingent of Brewers fans make the trip from Wisconsin to Wrigley Field which has seen a shift from Cub-fan dominance at games.

Despite being a new rivalry, the divisional rivalry is creating history on the field with the two facing off in a Game 163 tiebreaker to decide the National League Central division in 2018. The Brewers went on to beat the Cubs to become the top seed in the National League that year.

3. St. Louis Cardinals vs. Chicago Cubs

The Chicago Cubs keep popping up on our list and it’s little wonder, as they’re also one of the most popular MLB teams. The St Louis Cardinals vs. Chicago Cubs share a bitter rivalry that began in 1901 when the Cubs were known as the Orphans. In earlier years the Cardinals-Cubs game was known as the Route 66 Series, and more commonly referred to as the Downstate Illinois or I-55 Series. 

Historically the Cubs and Cardinals have fought for fan territory throughout the Upper West and Central Illinois which has divided friends and family. Before expansion of the MLB the Upper West states heavily supported the Cubs, and the Southern states followed the Cardinals.

Although the Cubs lead all time head-to-head, St. Louis has been far more successful overall winning 11 World Series titles. The Cubs have only managed three of their own.

The Cardinals-Cubs game created one of the most exciting league finishes ever during the 1998 season. The McGwire-Sosa home run chase went back and forth for months.

St Louis’ Mark McGwire and Chicago’s Sammy Sosa would run down Roger Maris’ 37-year single season home run record of 61. McGwire finished the season with 70 runs and Sosa was close behind on 66.

Many of the best players in MLB history have played in the Cardinals-Cubs game including Hall of Famer Rogers Hornsby, who many consider to be among the best hitters in history. Hornsby has played, as well as managed both the Cardinals and Cubs.

2. LA Dodgers vs. San Francisco Giants

The Dodgers-Giants game is one of the biggest MLB rivalries of all time and is one of the greatest rivalries in sports. It all began back in 1890 when both teams were based in New York. Based out of Manhattan, the Dodgers were originally known as the Bridegrooms and had a largely elitist fan base.

At the time, the Giants were based out of Brooklyn and were made up of many working class fans. In 1957 the Dodgers moved to LA and the Giants moved to San Francisco a year later. What was once an East Coast rivalry had transformed into a West Coast rivalry.

The Dodgers-Giants rivalry is now a battle between the “chilled out” Northern Californians and “sophisticated” Southern Californians. Despite these heavyweights playing each other more than 2,500 times the rivalry has been remarkably tight.

The teams have had a long history of eliminating each other from playoff contention and are moments that are considered precious to their respective fan bases. Amazingly it took until 2021 for the Dodgers and Giants to play each other in the postseason which was the first time in the 131-year rivalry, with the Dodgers winning the series 3-2.

1. New York Yankees vs. Boston Red Sox

The biggest MLB rivalry is between the New York Yankees and the Boston Red Sox. Regardless of the form of either of these sides the Yankees-Red Sox game is one of the most watched MLB games. For the majority of the rivalry the Yankees have dominated the fixture.

It was one moment however that changed the course of history for both franchises and led to an 86-year World Series title drought. Babe Ruth, the greatest baseball player of all-time, was traded from Boston to New York in 1919. The Yankees have gone on to win 27 World Series. The Red Sox? 9.   

Connecticut is considered to be the territorial battle line which separates fan support for the two teams and the rivalry has also spilled over into politics. Former mayor of New York City and Yankees fan Rudolph Giuliani openly professed his support for the Red Sox during the 2007 World Series much to the anger of fans in New York. 

Giuliani’s successor Michael Bloomberg who grew up a Red Sox fan from Boston, amazingly switched his allegiance to the Yankees after taking office.

The Yankees-Red Sox rivalry can get out of hand and has often led to violence between both sets of supporters. A Yankees fan was charged and convicted for reckless second-degree murder in 2008.

Matt Ieriko

Matt Ieriko is a freelance writer who’s evolved his lifelong passion for sport into the creation of WolfgangSport.com in 2020 – an American sports blog covering the NBA, NFL, MLB, NHL, MLS and more. As an Australian, he’s always been fascinated with the cultural differences and global significance of sports in America.

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