Top 10 Defining Playoff Moments of the Yankees–Red Sox Rivalry
NEW YORK – The New York Yankees and Boston Red Sox rivalry has always been about more than baseball. It has been about personalities, heartbreaks, curses, collapses, and unforgettable comebacks. With the two franchises clashing again in this year’s best-of-three wild-card series, we look back at 10 playoff (and playoff-adjacent) moments that defined one of sports’ greatest rivalries.
1. 2003 ALCS: Pedro, Grady and Boone
Game 7 at Yankee Stadium remains one of the most painful memories in Boston history. After Red Sox manager Grady Little left Pedro Martinez in the eighth inning, the Yankees stormed back to tie the game. In the 11th, Aaron Boone launched his walk-off homer, sending New York to the World Series and leaving Boston devastated.
2. 2004 ALCS: The Greatest Comeback Ever
Down 3-0 in the series, the Red Sox stunned the baseball world. Dave Roberts’ famous steal sparked the Game 4 rally, and David Ortiz delivered clutch hits in back-to-back extra-inning wins. Boston completed the historic comeback in Game 7 with a 10-3 victory, then swept St. Louis to end the “Curse of the Bambino.”
3. 1978 Tiebreaker: Bucky Bleepin’ Dent
With the AL East deadlocked at 99 wins, the Yankees and Red Sox met at Fenway Park for a one-game playoff. Light-hitting shortstop Bucky Dent homered over the Green Monster, sealing New York’s 5-4 win. For generations of Boston fans, his name still stings.
4. 2004: Varitek vs. A-Rod
On July 24, Jason Varitek shoved his catcher’s mitt into Alex Rodriguez’s face, igniting a benches-clearing brawl. The Red Sox rallied to win the game off Mariano Rivera, and many point to that moment as the spark that led to Boston’s eventual championship run.
5. 1973: Fisk vs. Munson
In a pennant race clash, Yankees catcher Thurman Munson barreled into Carlton Fisk at home plate, setting off a wild fight. The incident crystallized the bitterness between the two teams, with both star catchers embodying their clubs’ grit and pride.
6. 1999 ALCS: First Playoff Meeting
Despite decades of history, the rivals had never met in October until 1999. The Yankees prevailed in five games, with Bernie Williams’ walk-off in Game 1 and Pedro Martinez’s Game 3 dominance standing out. The Yankees would go on to win their second of three straight World Series titles.
7. 2018 ALDS: Boston’s Best Team Ever
The 108-win Red Sox dispatched the Yankees in four games, punctuated by a 16-1 blowout at Yankee Stadium. They went on to win the World Series, their fourth since 2004, cementing themselves as baseball’s new powerhouse.
8. 1949: Yankees Take the Pennant
With the Red Sox needing just one win in the final two games at Yankee Stadium, the Yankees swept the series in front of massive crowds. Joe DiMaggio, playing through pain, helped New York capture the pennant and start a dynasty that produced five straight World Series titles.
9. 2002: The “Evil Empire” is Born
When the Yankees outbid Boston for Cuban pitcher Jose Contreras, Red Sox president Larry Lucchino famously branded New York the “Evil Empire.” The label stuck — and perfectly reflected the rest of baseball’s disdain for the Yankees’ spending power.
10. 2021 Wild Card: A Lump of Cole
In the most recent postseason meeting, the Red Sox knocked Yankees ace Gerrit Cole out in the third inning at Fenway Park en route to a 6-2 win. Boston advanced past Tampa Bay before falling in the ALCS, while the Yankees were left with more October frustration.
A Rivalry Reignited
Though both clubs have endured ups and downs in recent years, a playoff clash between the Yankees and Red Sox still carries a weight unlike any other. From Ruth to Jeter, from Williams to Ortiz, the rivalry has produced baseball’s most unforgettable theater.
And as this year’s October chapter begins in the Bronx, one thing is certain: history is watching.
