The Most Shocking World Series Upsets in MLB History

The ghosts of October baseball are making their presence known, as heroes are born and rivalries are formed in the Major League Baseball postseason. All roads lead to the World Series, with the 2024 “Fall Classic” serving as the 120th edition of the event.

A couple of powerhouses in the Los Angeles Dodgers and New York Yankees remain standing, which also leaves open the possibility for a stunning upset in the World Series. Of course, that would be far from the first time something like that has happened.

1. New York Mets over Baltimore Orioles (1969)

The 1962 New York Mets lost 140 games in their inaugural season. To be in the World Series seven years later? Nothing short of miraculous.

That’s why the 1969 are lovingly known as the “Miracle Mets.” The team had lost at least 100 games in five of their previous seasons of existence, but took advantage of the expanded playoff system in 1969 and won 100 games. New York lost Game 1 of the series 4-1, but used elite starting pitching from Jerry Koosman and Tom Seaver to silence the Orioles’ bats the rest of the way. They celebrated their first title with a 5-3 win at Shea Stadium in Game 5, completing one of the most unlikely franchise turnarounds in baseball history.

2. Arizona Diamondbacks over New York Yankees (2001)

The mighty New York Yankees won the 1996, 1998, 1999, and 2000 World Series with relative ease. So an appearance in the 2001 “Fall Classic” would make a win more or less a formality, right?

Not exactly. The Arizona Diamondbacks were fueled by two aces in Randy Johnson and Curt Schilling, alongside a 57-home run-hitter in Luis Gonzalez. The Diamondbacks dominated the first two games, before the mystique and aura of Yankee Stadium struck. Three dramatic home runs saw New York take a 3-2 series lead with Games 6 and 7 going down in Arizona. The Diamondbacks won Game 6 15-2, and took Game 7 on the back of heroic pitching efforts from Schilling and Johnson, alongside a walk-off single from Gonzalez.

3. Cincinnati Reds over Oakland Athletics (1990)

The Oakland Athletics were an absolute powerhouse in the late 1980s into the early 1990s, aided by big bats and dominant pitching. They won the American League in 1988 and 1989, took the World Series crown in the ladder, and were poised to do the same in 1990.

Unfortunately for them, they ran into the Cincinnati Reds. The Reds were extremely deep with their “Nasty Boys” bullpen, while starter (and eventual World Series MVP) José Rijo was dominant in two starts for Lou Piniella’s squad. Oakland struggled at the plate, failing to put up more than four runs in any of the games in the series. The Reds swept the Athletics, shocking the baseball world.

4. Florida Marlins over New York Yankees (2003)

Even after the 2001 World Series loss, the Yankees seemed like perennial contenders for another championship. They won 101 games in 2003, and clinched a spot in the World Series in dramatic fashion when Aaron Boone hit a walk-off home run in Game 7 of the ALCS against the Boston Red Sox.

The Florida Marlins, meanwhile, just happened to be the hottest wild card team in baseball history. They started the season 19-29, but rallied to win 91 games and squeak into the postseason. The Marlins outbattled the heavily favored Atlanta Braves and Chicago Cubs en route to facing New York, then shocked Goliath when it mattered most. Josh Beckett, Miguel Cabrera, Dontrelle Willis, and Carl Pavano locked down the Yankees, and Florida won its second World Series in six games.

5. Washington Nationals over Houston Astros (2019)

Superstar outfielder Bryce Harper left the Washington Nationals in the 2019 offseason, dealing a devastating blow to both the franchise and fan base. They responded by starting the season 19-31, and it seemed like manager Dave Martinez was on the hot seat. Washington turned its season around and won 93 games though, finding its way to the World Series as a wild card.

The Houston Astros won the 2017 World Series title and were poised for another in 2019 with 107 regular season wins. But they were not prepared for what the World Series would bring: each team won on the road. The Nationals scored just three runs at home, but marched into the hostile Minute Maid Park and captured a World Series championship thanks to Game 7 heroics from Howie Kendrick. It was the first in franchise history.

6. Los Angeles Dodgers over Oakland Athletics (1988)

The 1988 Oakland Athletics were perhaps even more stacked than the team that would win the World Series the following season. Mark McGwire and José Canseco made up the iconic “Bash Brothers” tandem that mashed Oakland to the top of most offensive categories that season. Dave Stewart won 20 games for the team, while Bob Welch and Storm Davis contributed 17 and 16 respectively.

The Los Angeles Dodgers, on the other hand, didn’t have even one player hit .300 or drive in 90 runs. Yet the gritty group mustered their way to the World Series, and a baseball legend was born. Kirk Gibson smacked a game-winning pinch-hit home run off of Dennis Eckersley on virtually no leg power, a moment etched in time as an all-time great World Series moment. Tommy Lasorda’s team took the series 4-1, the last Dodgers World Series title before the COVID-shortened 2020 season.

7. New York Giants over Cleveland Indians (1954)

The Cleveland Indians were one of the most dominant American League teams to ever play during the 1954 season. They won 111 games in a 154-game season, and prevented the Yankees from reaching the World Series for the first time in five seasons. Cleveland pitchers threw 77 complete games that year, and the team was a heavy favorite against the New York Giants.

The Giants had a young man named Willie Mays. New York won Game 1 because of his all-time great catch in center field that quelled a potential Cleveland rally. The Giants would pull off an unexpected four-game sweep, scoring 21 runs over the four games off the stellar Cleveland rotation.

8. Kansas City Royals over St. Louis Cardinals (1985)

The “Show-Me” Series is a memorable one for all midwestern baseball fans, as the St. Louis Cardinals looked to be in full command of the Kansas City Royals when they were up 3-1.

The Royals cut the lead to 3-2, but trailed 1-0 in the bottom of the ninth inning in Game 6. Jorge Orta hit a ground ball to first baseman Jack Clark, and Cardinals pitcher Todd Worrell ran to cover first. Worrell got the feed from Clark and stepped on the bag, but first base umpire Don Denkinger ruled Orta safe. Replays and photos showed Orta was indeed out, but the Royals would rally and win the game 2-1. They won Game 7 11-0, and pulled off an improbable comeback over the Cardinals.

9. Pittsburgh Pirates over New York Yankees (1960)

The Yankees were an offensive juggernaut in 1960, with the likes of Mickey Mantle and Yogi Berra blasting New York to the World Series against the Pittsburgh Pirates.

What would follow would be a total anomaly of a series. The Yankees would put up 55 runs across seven games, outsourcing the Pirates 55-27. They scored more than 10 runs three times in the series, but struggled to string together four wins. Pittsburgh forced a Game 7 at home, and led late 9-8. The Yankees would tie the game in the ninth inning, and in the bottom of the frame, Bill Mazeroski stepped to the plate for Pittsburgh. He skied one over Yogi Berra’s head in left, and the Pirates won the series in dramatic fashion.