Top 10 Wildest World Series Upsets of All Time

Winning a World Series is no easy task, even for a team that is filled with star players. To do so, a side has to survive a gruelling 162-game season, and it then has to avoid multiple playoff letdowns just to qualify for the Fall Classic.

Thus, World Series upsets are not uncommon.

It was inevitable that some historic upsets were going to be left off of this list. Certain teams and certain years stick with a person more so than do others. That's human nature. Odds are that age, whether I realized it or not, likely also played a role in the creation of this piece. I've only been watching baseball for three decades, after all.

Regardless, feel free to weigh in with your opinions in the comments section below. Now sit back and reminisce as we recap 10 of the greatest World Series upsets of all time.


10 Arizona Diamondbacks vs. New York Yankees - 2001

Sports often serve as a soothing and healing outlet following a tragedy, and that was seemingly to be the case in the fall of 2001. One month after the horrific events of September 11, the Yankees went on a magical run, one that saw them win the American League championship and punch a ticket to meet the Diamondbacks in the World Series.

As millions of people in the NYC region and around the country who were rooting the Yanks on found out, sports can also break hearts. The Yankees swept all three games held in the Bronx, but they were then routed 15-2 in Game 6. Then, with New York three outs away from winning it all, the unthinkable occurred, as Mariano Rivera couldn't close the D-Backs out. Arizona scored twice in the final frame of the World Series to win 3-2, and the crowd at Bank One Ballpark erupted in celebration.

I found it difficult to rank this Series. After all, it isn't as if that Diamondbacks team didn't have a lot of talent. Everything just seemed to be tilted toward the Yankees winning that Series, but fate was cruelly not on their side.

9 Boston Braves vs. Philadelphia Athletics - 1914


The mere thought of the Braves making the World Series in the summer of '14 would have been laughable. In dead last on Independence Day, Boston won over 78 percent of the remaining games on their schedule. Boston then made short work of the A's, sweeping Philadelphia to win the Series.

This Series would be ranked higher up on this list if not for the speculation that at least some on the Philadelphia roster phoned those games in due to the rocky relationship they had with manager Connie Mack. It's also been suggested that some players may have been paid off to throw the Series.

8 Cincinnati Reds vs. Oakland Athletics - 1990

The A's were the defending champs. They easily won the division, and then swept the Boston Red Sox in the ALCS. Oakland had the “Bash Brothers” in Jose Canseco and Mark McGwire. This was supposed to be a bloodbath, a sure-thing for the A's.

Not only did that not occur, but the Reds dominated the Series. They won the first game 7-0, and, from there, Cincy swept Oakland right out of the Series and a spot in history. It could, all things considered, be the most-shocking sweep ever to occur in any MLB postseason.

7 St. Louis Cardinals vs. Detroit Tigers - 2006


The Cards weren't even supposed to be in the '06 World Series. St. Louis, a team that won 83 regular season games, could not, on paper, hang with the New York Mets in the NLCS. The Cardinals didn't just hang. They shocked the Amazin's, winning that series 4-3 and clinching a World Series berth while at Shea Stadium.

Those on the Tigers were their own worst enemy on baseball's biggest stage. They committed an error in every game of the Series. Detroit barely looked like a playoff team let alone one playing for a championship. The 4-1 St. Louis victory made for, outside of those cheering the Cards on, one of the more forgettable Fall Classics of recent memory.

6 Florida Marlins vs. New York Yankees - 2003

This Series was, for anybody who hated/hates the Yankees, one that the ages. Florida's young team, one very highly over-matched on paper and one that had a payroll of $54 million, faced off against the Evil Empire, everything supposedly wrong with the game. Having a payroll of $164, the Yankees had, in the eyes of many, bought themselves a championship before the Series even began.

Somebody forgot to inform the Marlins.

Florida split the first two games of the Series before winning two of three at home. Josh Beckett out-duelled Andy Pettitte in the sixth and deciding game, and the Marlins danced on the Yankee Stadium field as many in the crowd watched in silence.

5 New York Giants vs. Cleveland Indians - 1954


There was once a time where Cleveland was the home to multiple professional sports champions. Six years after winning the World Series, the Tribe won 111 games, and they were heavily favored to defeat the Giants and do so easily.

That, as the saying goes, is why they play the games.

This Series will forever be remembered by the spectacular over-the-shoulder catch made by Willie Mays, arguably the greatest defensive play to ever occur in a Fall Classic. Cleveland never recovered from that magical moment, and the Giants went on to sweep the Indians.

The city of Cleveland had to wait 41 years before the Indians again made it to a World Series. The Tribe still hasn't won a title since '48.

4 Chicago White Sox vs. Chicago Cubs - 1906

That the '06 White Sox made the World Series goes to show just how different the league was way back when. The so-called “Hitless Wonders” had a .230 batting average. They hit .198 in a Series that was, on paper, the Cubs' to lose.

Lose the Cubbies did, and in somewhat shocking fashion. The White Sox exploded for eight runs in both Games 5 and 6 to turn a tied series into a 4-2 win in their favor. Forgotten in history is that the Cubs won over 76 percent of their regular season games that year, something that is unheard of these days.


3 Pittsburgh Pirates vs. New York Yankees - 1960


Bobby Shantz. Elston Howard. Roger Maris. Yogi Berra. Mickey Mantle. The Yankees entered the '60 World Series with more big names on the roster than on that of the Pirates. New York thrice put double-digit runs on the scoreboard against the Pirates. Two of those games occurred at Forbes Field in Pittsburgh.

The Buccos would, however, not be deterred. Pittsburgh won two straight at Yankee Stadium, and then, after getting crushed in Game 6, the Pirates couldn't hold a lead in Game 7. With the scored tied at nine to start off the bottom of the ninth, Bill Mazeroski launched the first World Series-winning home run in the history of Major League Baseball, and the Pirates, thoroughly outplayed for much of the Series, were champions.

2 Los Angeles Dodgers vs. Oakland Athletics - 1988

Game 1 of the '88 World Series is responsible for one of my favorite moments that was highlighted in Ken Burns' Baseball documentary. Kirk Gibson, LA's leader on and off the field, had injured both legs in the prior NLCS, and he was also battling a stomach bug when he was called to pinch-hit in the bottom of the ninth of the Series opener.

With two outs and a runner on, Gibson worked the at-bat to a full count before launching a Dennis Eckersley slider over the right field wall for the walk-off win. Gibson's lone at-bat of the World Series propelled the underdog Dodgers to a 4-1 Series win, and that hit remains one of the most memorable moments to ever occur in a Fall Classic.

1 New York Mets vs. Baltimore Orioles - 1969


Perhaps I ranked this one too high due to my being a fan of the Amazin's, but the Miracle Mets are, for me, one of the great stories in the history of North American professional sports. The Mets had never even flirted with a winning record in their first eight seasons of existence. Nobody outside of diehard Mets fans deemed to be in denial gave New York a chance of doing anything of note at the start of the '69 season.

Then came the final month and a half of the season, during which the Mets got hot and ultimately finished with a regular season record of 100-62. The Orioles, winners of 109 regular season contests, couldn't have known that they didn't stand a chance. Baltimore won the Series opener before dropping four straight, a team always destined to be on the wrong side of history.


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