6 Biggest World Series Upsets in MLB History

| October 13, 2021 1:50 pm PDT

Who doesn’t love a good underdog story? Throughout baseball history, we’ve seen teams defy the odds and win the World Series.

A lot of times, it’s surprising to see the team even make the World Series. Once there, they have a chance to shock the world.

America’s pastime has had quite a few World Series upsets. Let’s look at six World Series that saw unexpected outcomes.

6. St. Louis Cardinals Over Detroit Tigers (2006)

Nothing about the 2006 St. Louis Cardinals screamed World Series contender. They had an average offense and allowed the second-most runs among playoff teams.

It certainly didn’t help that they went 25-36 to close the season. That gave them an overall record of 83-78.

On the other side, the Detroit Tigers finished an AL-best 95-67. Anchored by a rotation that included Justin Verlander and Kenny Rogers, the Tigers allowed the fewest runs in the majors.

The Cardinals went on pull-off major upsets over the San Diego Padres and MLB best New York Mets to make the World Series. Detroit defeated the New York Yankees and Oakland Athletics on their way to the World Series.

Not many people gave St. Louis a chance in the World Series. They had a nice run but everyone expected it to come to an end. Well, everyone except the Cardinals.

A pair of home runs led the Cardinals to a Game 1 victory. Detroit bounced back with a 3-1 victory in Game 2.

In his postseason debut, Cardinals pitcher Chris Carpenter pitched eight shutout innings in the Cardinals 5-0 win.

Game 4 saw the Tigers take an early 3-0 lead, but the Cardinals took their first lead in the seventh inning. After the Tigers tied it, the Cardinals scored the go-ahead run in the bottom of the eighth to take a commanding 3-1 series lead.

St. Louis won their first World Series with a 4-2 victory in Game 5. Future ace Adam Wainwright recorded the game’s final out.

David Eckstein went on to win MVP after hitting .364 with four RBIs and three doubles.

Their 83-78 record stands as the worst for a World Series champion. But hey, it’s not about how you start, it’s about how you finish.

5. Pittsburgh Pirates Over New York Yankees (1960)

Do you know all those legends your parents and grandparents tell you about? Yeah, most of them were on this New York Yankees team.

A roster that featured guys like Mickey Mantle, Yogi Berra, Roger Maris, Bobby Shantz, and Elston Howard led the Yankees to an AL-best 97-57 record.

Maris went on to win MVP with these numbers.

  • .283 batting average
  • 39 home runs
  • 112 RBIs

The Pittsburgh Pirates weren’t bad by any means. They finished the season 95-59-1 with a guy by the name of Roberto Clemente. Even with the great season, the Pirates went into the World Series as big underdogs.

How on Earth would the Pirates knock off the powerful Yankees?

Pittsburgh won Game 1, but New York responded with a pair of blow-out victories. Facing a potential 3-1 series deficit, the Pirates pitching shut down the Yankees offense to tie the series.

In Game 5, the Pirates defeated the Yankees to give them a chance to clinch the series at home. However, New York forced a game 7 with their third blowout victory of the series.

Game 7 proved to be a wild back-and-forth affair.

New York held a 7-4 lead going into the bottom of the eighth inning. That’s when the Pirates rattled off five runs to take a 9-7 lead into the ninth. New York tied the game with a pair of ninth-inning runs.

Bill Mazeroski hit a walk-off home run to give the Pirates a 10-9 victory and World Series title. It was the first time in MLB history a home run ended the World Series.

When you look at the run differential, you would never believe the Pirates won the series. The Yankees three blowout victories gave them a 55-27 edge in run differential.

At the end of the day, the Pirates won four games and the Yankees only won three.

4. Cincinnati Reds Over Oakland Athletics (1990)

This matchup wasn’t necessarily a good team vs a bad team, as much as a great team vs a good one.

The Oakland Athletics finished with the best record in baseball for the third straight season. They were looking to win the AL Pennant for the third year in a row.

Oakland had so much success because of their potent offense and elite pitching staff. Ricky Henderson won the AL MVP after hitting .325 with 28 home runs and 61 RBIs. Mark McGwire and Jose Canseco slugged 39 and 37 home runs, respectively.

These guys were household names in the late 80s and early 90s.

Their pitching staff featured AL Cy Young winner Bob Welch. He and Dave Stewart led an elite Athletics rotation.

Bob Welch Dave Stewart
Record 27-6 22-11
ERA 2.95 2.56
Strikeouts 127 166

The Cincinnati Reds finished with a 91-71 record. The “Nasty Boys” consisted of a trio of elite bullpen pitchers. Their success played a big hand in the Reds march to the World Series.

Oakland swept the Boston Red Sox to advance to their third straight World Series. Cincinnati took down the Pittsburgh Pirates in an NLCS that had four one-run games.

Just about everyone expected Oakland to take care of business and win their second consecutive World Series title. However, the Reds came to play.

Cincinnati won 7-0 in Game 1, and took a 2-0 series lead after a walk-off single in the 10th inning. The series shifted to Oakland but it didn’t do much for the Athletics. A seven-run third inning propelled the Reds to a commanding 3-0 series lead.

In Game 4, the Reds scored two runs in the eighth inning to take a 2-1 lead. Their bullpen finished the job to give Cincinnati a four-game sweep.

The Athletics lethal offense had nothing for Cincinnati’s pitching. They scored just eight runs in the series.

3. Florida Marlins Over New York Yankees (2003)

If you ever wonder about the meaning of David vs. Goliath, just look at the 2003 World Series.

The Florida Marlins came into the season with one of the lowest payrolls. The team fired their manager early in the season and their record was as bad as 19-29.

Florida went on to finish 91-71 behind 72-year-old manager Jack McKeon.

On the other side, the New York Yankees had the highest payroll and finished an MLB best 101-61.

Florida upset the defending NL pennant winner San Francisco Giants in the NLDS. They took down the Chicago Cubs with a little help from Steve Bartman.

New York had a memorable seven-game ALCS against the Boston Red Sox. They scored three runs in the bottom of the eighth in Game 7 to send it to extras. Aaron Boone hit a walk-off home run in the 11th to send New York to the World Series.

The Marlins had a nice run but no one expected them to hang with the Yankees. That became even more prevalent when the Yankees jumped out to a 2-1 series lead.

Even so, the Marlins wouldn’t go quietly. They walked off in the 12th inning in Game 4 and took a 3-2 series lead with a 6-4 victory in Game 5.

Game 6 featured a pitcher’s duel between Josh Beckett and Andy Pettitte. Pettitte blinked first, allowing a run in the fifth. The Marlins would add another in the sixth.

That was all Beckett needed. His complete-game shutout clinched the World Series for the Marlins.

Here are his numbers from Game 6.

  • 9.0 innings
  • 5 hits
  • 2 walks
  • 9 strikeouts

Just like they did in 1960, the Yankees lost the series despite outscoring their opponent.

This World Series showed you don’t need to have big named players to win it all.

2. Los Angeles Dodgers Over Oakland Athletics (1988)

The Oakland Athletics were on the brink of a dynasty in 1988. Behind the “Bash Brothers,” Oakland finished with the best record in baseball at 104-58.

Jose Canseco and Mark McGwire made up the Bash Brothers, with Canseco claiming the AL MVP. He did so with these impressive numbers.

  • .307 batting average
  • 42 home runs
  • 124 RBIs
  • 40 stolen bases

He became the first player in MLB history to post 40 home runs and 40 stolen bases in the same season.

The Los Angeles Dodgers didn’t have an imposing offense, but their rotation featured three pitchers with an ERA below 3.00. That included NL Cy Young winner Orel Hershiser. Los Angeles finished with a 94-67 record.

Oakland swept the Boston Red Sox to qualify for the World Series. The Dodgers pulled a big upset, defeating the New York Mets in seven games in the NLCS. New York had won 10 of 11 games against the Dodgers in the regular season.

Game 1 of the World Series ended with Kurt Gibson’s iconic home run. Los Angeles took a 2-0 series lead behind a complete-game shutout from Hershiser.

McGwire’s walk-off home run gave the Athletics their first win of the series.

Los Angeles may not have had a lot of offense, but their pitching closed the door. They won games 4 and 5 to clinch the World Series.

Hershiser concluded his legendary season with a complete game. This shouldn’t surprise anyone but he went on to win World Series MVP.

Just like the 1990 World Series, Oakland’s offense had nothing for the amazing pitching staff. Oakland scored just 11 runs across the five games.

Everyone remembers the series for Gibson’s walk-off in Game 1. However, I think the real story is Hershiser and the Dodgers rotation shutting down a lethal Athletics offense.

1. New York Mets Over Baltimore Orioles (1969)

Coming into the 1969 season, I can’t imagine many people expected the New York Mets to compete for a playoff spot. Since joining the NL in 1962, they had never won more than 73 games.

The Mets started 18-23, but they went on an unprecedented 82-39 run to end the season with a 100-62 record.

The Baltimore Orioles cruised through the 1969 season. They finished 109-53, finishing 19 games ahead of the Detroit Tigers in the AL East. Baltimore had one of the greatest rotations in MLB history that season.

Record ERA Strikeouts
Jim Palmer 16-4 2.34 123
Mike Cuellar 23-11 2.38 182
Dave McNally 20-7 3.22 166
Tom Phoebus 14-7 3.52 117

Their offense wasn’t too shabby either with Boog Powell, Frank Robinson, and Brooks Robinson.

Each team swept their way to the World Series. With all their firepower, Baltimore entered the World Series as massive favorites. That only grew when they won Game 1.

However, Baltimore’s offense went ice cold. They dropped the ensuing three games, scoring a combined two runs. It didn’t matter that their pitching held the Mets to two runs in games 2 and 4.

In Game 5, Baltimore’s offense woke up, as they took a 3-0 lead. This time, it was their pitching that let them down.

New York scored five runs from the sixth to eighth inning. They hung on to win 5-3 and win the World Series. The title earned them the nickname “Miracle Mets.”

There are a lot of people who view this as one of the biggest upsets in sports history. Coincidentally enough, this was the same year the New York Jets upset the Baltimore Colts in Super Bowl III.

It’s clear 1969 did not work out well for Baltimore teams. New York probably can’t get enough of that year.

Other Big World Series Upsets

  • Boston Braves Over Philadelphia Athletics (1914)
  • Baltimore Orioles Over Los Angeles Dodgers (1966)

The Boston Braves were left for dead in early July. They were in last place before ending the season 70-19. From there, the “Miracle Braves” swept the Philadelphia Athletics in the World Series.

In 1966, the Los Angeles Dodgers had an elite rotation led by Sandy Koufax. However, their offense scored a combined two runs in the Baltimore Orioles’ four-game sweep.

For the most part, the best team wins the World Series. However, there are years where we have a surprise winner and the lovable underdog pulls through.

We went way back for a few upset winners. Check out some of the top stars from the 1940s to 1980s.

Nicholas Sterling
Nicholas Sterling

Nicholas has been a Sports Writer with GamblingSites.com since May 2021. He has a rich sports background, writing about NASCAR, NFL, NBA, MLB, NHL, Golf, etc. Nick is always ready for a new challenge.

He enjoys rooting on D.C. sports teams, including the Commanders, Wizards, and Capitals.

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