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The Grueling Truth - Where Legends Speak / Top 9 Greatest World Series Upsets of All Time

Top 9 Greatest World Series Upsets of All Time

Greatest World Series Upsets
Publish Date: 08/12/2023
Fact checked by: Simon Briffa

Top 9

The World Series has a long history of surprises, and today we are going to take a look at the greatest surprise of all, the UPSET!

9) 1906 Chicago White Sox vs Chicago Cubs

That the ’06 White Sox even made the World Series shows how different the league was at the turn of the twentieth century. The so-called “Hitless Wonders” had a .230 team batting average. Instead, they hit .198 in a Series that was, on paper, the Cubs should have never lost.

Lose the Cubbies did and in a somewhat shocking fashion. The White Sox exploded for an incredible eight runs in games 5 and 6 to turn a tied series into a 4-2 win in the Sox favor. Forgotten in history is that the Cubs won a shocking 76 per cent of their regular-season games that year, which is unheard of in this day and age.

Video: 1906 World Series Game 1: White Sox @ Cubs

1906 World Series Game 1: White Sox @ Cubs

8) 1954 Cleveland Indians vs New York Giants

The Tribe won 111 games in 1954 and was heavily favored to defeat the Giants and do so quickly. Remember back in the ’50s, the city of Cleveland was used to winning championships; the Indians in 1948, and the Browns won multiple titles.

This Series will forever be remembered by the spectacular over-the-shoulder catch made by Willie Mays, one of the greatest defensive plays in World Series history. Unfortunately, Cleveland never recovered from that incredible moment, and the Giants swept the Indians handily.

Video: 1954 World Series

1954 World Series

7) 2006 Detroit Tigers vs St.Louis Cardinals

The Cardinals won the NL Central in 06 with a less than spectacular 83-78 record. The Detroit Tigers won 95 games that year and defeated the Yankees, and A’s to reach the Fall Classic. The Tigers had seven players with at least 16 homers, led by Craig Monroe’s 28. The Tigers were led by great pitching, helped by rookie Justin Verlander (17-9) and veterans Kenny Rogers (17-8), and Jeremy Bonderman (14-8).

The Cardinals knocked out the Padres in the Division Series, then won a thrilling 7-game NLCS over the Mets, who racked up a league-best 97-65 mark. Yadier Molina’s two-run, ninth-inning homer in Game 7 broke open a 1-1 tie, and closer Adam Wainwright fanned Carlos Beltran looking for the final out. The Mets were heavy favorites to win it all.

The Tigers pitching staff fell apart in the Series, committing five errors. Meanwhile, Series MVP David Eckstein (.364) was one of the several unlikely heroes for St. Louis, which also got great performances from pitchers Anthony Reyes and Jeff Weaver. The Cardinals’ 83-78 regular-season record is the worst by a World Series champ.

Video: 2006 World Series Film-Full

2006 World Series Film-Full

6) 1914 Boston Braves vs Philadelphia A’s

The Boston Braves were in last place on July 4, then rolled off a 70-19 record to win the National League by 10.5 games.

They met the great Philadelphia Athletics, who racked up 99 wins under future Hall of Fame manager the great Connie Mack. The A’s had won three of the previous four Series. But the Braves were not intimidated.

Boston swept Philadelphia, outscoring the A’s, 16-6. After the embarrassing defeat, Mack reacted by selling or trading a majority of the players from his team. Hall of Fame second baseman Eddie Collins was one of the unlucky souls dealt; Collins had won the MVP that year, he was sold to the White Sox.

Video: 1914 World Series

1914 World Series

5) 1990 Cincinnati Reds vs Oakland A’s

If you look back at these teams, it doesn’t seem like that big of an upset. At the time, though, nobody outside of Cincinnati gave the Reds any chance of winning this Series. The A’s had the Bash Brothers, Canseco, McGwire, etc… They had intimidating pitching led by starter Dave Stewart and closer Dennis Eckersley. The Reds beat Stewart 7-0 in game one of the Series; then, in game two, they took care of Eckersley in extra innings to go back to Oakland up two games to none.

In Oakland, the Reds domination of the A’s continued; game 3 was a dominant 8-3 win, and the Reds closed out game four 2-1 behind the outstanding pitching of Jose Rijo.

Video: 1990 WS Gm2: Oliver's single off Eckersley wins game

1990 WS Gm2: Oliver’s single off Eckersley wins game

4) 2003 Florida Marlins vs New York Yankees

In May, Florida opened the 2003 season, struggling mightily, and fired Jeff Torborg for veteran manager Jack McKeon. McKeon quickly turned the team around as he guided the Fish to a 75-49 record the rest of the way, grabbing the Wild Card, ten games behind Atlanta.

The Bronx Bombers won 101 games, backed by its stellar staff of Roger Clemens, Andy Pettitte, Mike Mussina, and David Wells. They were coming off an emotional ALCS win on Aaron Boone’s series-winning home run against the hated Sox. The Yankees had been in six of the last eight World Series, while the Marlins had won the 1997 World Series, but that team had long been disassembled.

The Marlins won the World Series behind the clutch pitching of Josh Beckett, Brad Penny, and Carl Pavano. Beckett threw a five-hit shutout to clinch the Series in Yankee Stadium.

Video: 2003 World Series Highlights

2003 World Series Highlights

3) 1960 World Series Pittsburgh Pirates vs New York Yankees

This had to be the most uneven World Series ever played. The invincible Yankees won three games by a combined 38-3 score, but the Pirates won all the close games, including a see-saw Game 7.

This Yankees 97-win team featured Mickey Mantle, Yogi Berra, Roger Maris, Moose Skowron, Elston Howard, and Whitey Ford. The Yankees during this period were considered by many to be invincible.

Still, the most iconic moment in series history has to be Bill Mazeroski’s lead off the bottom of the 9th home run that clinched the Series for the Pirates at Forbes Field.

Video: The World Series of 1960: New York Yankees vs Pittsburgh Pirates

The World Series of 1960: New York Yankees vs Pittsburgh Pirates

2) 1988 Los Angeles Dodgers vs Oakland A’s

This will always be known for the game one walk-off home run hit by a hobbled Kirk Gibson. However, many people forget the Dodgers pulled another upset to get to this Series when they defeated the New York Meta in seven games. The Mets were a high-powered team that was supposed to battle the A’s in the World Series.

Orel Hershiser took over after Gibson and pitched amazingly well against the vaunted A’s offense. He started and won a game, then closed out game five as a reliever.

Video: Kirk Gibson's legendary 1988 World Series walk-off home run, called by Vin Scully!

Kirk Gibson’s legendary 1988 World Series walk-off home run, called by Vin Scully!

1) 1969 New York Mets vs Baltimore Orioles

109-win Baltimore team featuring one of the finest rotations in baseball history with Jim Palmer, Mike Cuellar, Dave McNally, and Tom Phoebus.

After losing the first game of the series, the Mets got hot winning the next four, holding the Orioles to just five runs during the rest of the Series. Donn Clendenon was the Series MVP, batting an unimpressive .257 but with three homers, though it was more the Mets’ pitching staff, which held the vaunted Orioles offense to a .146 batting average. Seaver and Jerry Koosman were the only pitchers to surrender a run.

The Orioles had won 109 games in 1969, but this can happen when you run into pitching as the Mets had. Throw in the fact that the Mets made probably a half dozen amazing plays in the field behind the great pitching, and you have the formula for beating a great team.

Video: 1969 World Series Film New York Mets

1969 World Series Film New York Mets

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