Top 10 World Series Moments

Baseball fans in recent years have been lucky to see some of the best World Series moments on record. Who could forget the Chicago Cubs’ incredible rally in 2016 to end a 108-year drought? What about the Boston Red Sox and Los Angeles Dodgers’ thrilling 18-inning battle in 2018? The baseball season seemingly always finds a way to finish with a flourish.

The World Series has existed since 1903, providing some of the most iconic baseball moments in the process. We’ll see what this year’s Fall Classic offers up, especially if New York Yankees superstars Aaron Judge and Juan Soto lead the Bronx Bombers to their first pennant since 2009. 

Best World Series Moments of All Time

So, what are the best World Series moments in MLB history? For this list, we factored in the historical context, the players in question, and how epic we felt the plays in question truly were. We’re sure you’ll see some familiar highlights on this list, but make sure to let us know in the comments if there’s anything we missed. 

Are streaming services blocked on your school or office network? That doesn’t mean you have to miss out on any of the World Series games. ExpressVPN lets you unblock those streaming services and bypass ISP throttling so you can watch without buffering. Call us biased, but we say ExpressVPN is the best VPN for making sure you catch every pitch of the Fall Classic. 

Get ExpressVPN

Honorable mention: Babe Ruth’s called shot (1932)

Did Babe Ruth really call his shot during the 1932 World Series? Yes! The film of the Yankees’ Game 3 victory over the Cubs at Wrigley Field proves that the Bambino did, in fact, gesture to deep center field before homering off starting pitcher Charlie Root. However, historians have spent nearly a century arguing the intent behind Ruth’s pointing. Was Ruth taunting Root and promising he’d take the ace deep, or was he simply signaling to the fans?

Whatever the case, Ruth makes our list as an honorable mention. There’s no denying the significance of Ruth’s called shot, a moment that has inspired everything from artwork to books. However, the iconic moment taking place in the pre-TV era slightly hurts its case here by no fault of its own. 

10. Kirby Puckett will see you tomorrow night (1991)

Minnesota sports teams have a habit of letting their fans down, a club Anthony Edwards and the Timberwolves rejoined during last year’s NBA playoffs. Once upon a time, though, Kirby Puckett and the Twins managed to win not one, but two World Series titles within a five season span. It’s the second of those championships, a seven-game victory over John Smoltz’s Atlanta Braves in 1991, that remains immensely memorable.

After robbing Ron Gant of a home run earlier in the game, Puckett stepped to the plate in the bottom of the 11th. Originally intending to bunt against reliever Charlie Leibrandt, Puckett instead launched a 2-1 pitch for a walk-off home run. CBS play-by-play announcer Jack Buck remarked, “And we’ll see you tomorrow night!” His son, Joe, has since used this line on other occasions. The Twins notched a 1-0 victory the next night, earning their second (and most recent) title in the process.

9. Joe Carter touches them all (1993)

Something was in the water during those World Series in the early 1990s. Two years after Gene Larkin ended the 1991 Fall Classic with a walk-off single against the Braves, Blue Jays outfielder Joe Carter had his own opportunity to make history. Facing Philadelphia Phillies All-Star closer Mitch Williams in a 6-5 game, Carter smashed a walk-off home run to left field, giving the Blue Jays their second straight championship.

Suffice to say, Phillies fans never exactly forgot Carter’s home run. The City of Brotherly Love hosted the 1996 MLB All-Star Game, and Carter, still representing the Blue Jays, heard no shortage of boos during pregame introductions.  

8. Don Larsen’s perfect game (1956)

As longtime New York Daily News reporter Joe Trimble aptly put it, the imperfect man pitched the perfect game! A fourth-year right-hander who went an ugly 3-21 two seasons earlier for the Baltimore Orioles, Larsen—now a mainstay in the New York Yankees’ rotation—retired all 27 Brooklyn Dodgers he faced in Game 5 of the 1956 World Series.

Incredibly, Larsen’s perfect game marked the first no-hitter in MLB postseason history and remained so until Phillies ace Roy Halladay no-hit the Cincinnati Reds in 2010. As of 2024, no other pitcher has thrown a postseason perfect game. 

7. Cubs break the curse! (2016)

The Boston Red Sox and Chicago White Sox were the first to break their title droughts, ending respective 86- and 88-year schneids in 2004 and 2005. However, the Cubs kept waiting to hold the Commissioner’s Trophy, hitting an even 100 years without a championship in 2008.

Would the Cubs ever win a World Series again? Why yes, they would! Fittingly, Kris Bryant and the Cubs returned to the top of the heap against the Cleveland Indians, a team seeking its first title since 1948. The thrilling Game 7 in Cleveland featured everything from a game-tying home run from light-hitting Indians outfielder Rajai Davis to a 17-minute rain delay in extra innings. The Cubs took an 8-6 lead in the top of the 10th and, after allowing a run, held on to party in Cleveland.

The Indians, meanwhile, failed to win a title before rebranding as the Guardians in 2022. At some point, they’ll need to end the drought … right?

6. Bill Mazeroski shocks the Yankees’ dynasty (1960)

By the time the 1960s began, the cracks in the New York Yankees’ armor were starting to show. The Bronx Bombers failed to win the AL pennant in 1959, missing their first World Series since 1954. With the help of newly acquired outfielder Roger Maris, the Yankees returned to form and locked up their 25th pennant, setting up a World Series clash with the Pittsburgh Pirates.

Considered favorites to secure their ninth World Series title since 1947, the Yankees instead shockingly lost the series in seven games. Pirates second baseman Bill Mazeroski cemented his place in MLB history with a walk-off home run over Yogi Berra’s head in Game 7. Although the Yankees rebounded to win the next two World Series, the beginning of the end was near. Baseball fans can thank a Pirates team that triumphed in the Fall Classic despite being outscored 55-27 in the process!

5. Reggie Jackson becomes Mr. October (1977)

After losing in the 1976 World Series, the Yankees struck big in free agency and signed All-Star outfielder Reggie Jackson. Previously a three-time champion with the Oakland Athletics, Jackson overcame a feud with manager Billy Martin to help the Yankees return to the Fall Classic and face their longtime rivals, the now-Los Angeles Dodgers, yet again.

With the Yankees facing a clinching scenario in Game 6, Jackson swung the bat three times on a crisp October night. All three times, Jackson sent the ball into the stands, fittingly becoming the first player since Babe Ruth to hit three home runs in a World Series game. Christened “Mr. October” for his heroics, Jackson earned World Series MVP honors and a fourth championship ring. 

4. Derek Jeter becomes Mr. November (2001)

Derek Jeter remains arguably baseball’s most iconic player of the 21st century, a remarkable feat considering he last took an at-bat in 2014. By 2001, he was already a World Series MVP, a four-time champion, and the face of the most recent Yankees dynasty. 

Perhaps his most memorable moment came in the early hours of November 1, 2001. Not long after the Yankees improbably forced a tie game against Byung-Hyung Kim and the Arizona Diamondbacks, Jeter lined a walk-off home run to right field. Yankees radio announcer Michael Kay called Jeter “Mr. November,” referencing Jackson’s own nickname and a sign a Yankees fan held. 

You almost forget, then, that the Yankees eventually lost the 2001 World Series in seven games, but that’s a conversation for another day. We’re still stuck on Jeter being retired for a decade at this point…

3. Bill Buckner enters baseball immortality (1986)

Remember when we mentioned the Red Sox needed 86 years to break their World Series title drought? Red Sox fans of a certain age will remember thinking the streak would instead end after 68 years! Boston had a 5-3 lead in the 10th inning of Game 6 when the New York Mets slowly rallied and tied the game with two outs.

Mets star Mookie Wilson hit a ground ball up the first base line, setting up an easy play for veteran Bill Buckner to field the ball and, presumably, run it himself to the bag. Instead, the ball rolled through Buckner’s legs, giving the Mets a 6-5 lead and setting the stage for their 8-5 victory the next night. Good thing for 2004, right?

(Sorry, Yankees fans.)

2. Carlton Fisk waves it fair (1975)

Baseball fans can thank a rat, of all things, for Fisk’s home run earning the second spot on our list. In a 1999 interview, NBC cameraman Lou Gerard admitted a nearby rodent distracted him from following the ball Fisk smashed down the left field line in Game 6. Instead, the camera remained on Boston’s All-Star catcher as he tried willing the ball fair.

A waving Fisk got his wish, and the ball clanked off the left field foul pole for a game-winning home run. Unfortunately for Red Sox fans, Joe Morgan and the Reds eked out a 4-3 victory in Game 7 to take the series.

1. Kirk Gibson’s improbable, impossible home run (1988)

The underdog Dodgers faced a tough reality entering the 1988 World Series. Star outfielder Kirk Gibson, who led the club with 25 home runs and 31 stolen bases, injured both legs during an NLCS victory over the Mets. Officially called day-to-day, the All-Star was widely expected to miss the Fall Classic.

Somehow, Gibson mustered the strength to take the plate and work a 3-2 count against Athletics star closer Dennis Eckersley. Gibson famously drilled Eckersley’s slider over the right field wall for a walk-off home run and a Game 1 victory. Although Gibson didn’t play again in the series, the Dodgers managed to defeat the A’s in five games. 

Why you need a VPN to watch the World Series

Ever noticed that your connection seems to slow down whenever you start streaming? You could be the victim of activity-based ISP throttling. ExpressVPN encrypts your traffic so your ISP can’t see what you’re doing online and slow you down based on your streaming activity. You can live stream games securely in HD, or even UHD when available, with no lag or buffering.

Trying to stream on a restricted network? VPN encryption allows you to stream at school or even from the office. It also keeps your data safe on unsecured public Wi-Fi networks. If you have any questions about streaming the World Series with a VPN, our dedicated customer support team is online 24/7 to help you out.

Get ExpressVPN