The idea that familiarity breeds contempt is well-known, and it is illustrated throughout the history between the Boston Red Sox and the New York Yankees. Two of the most iconic teams in MLB history spent more than a century battling each other, producing countless heated matchups and endless highlight-worthy moments as each team tried to outdo the other. The five instances listed here have helped define the Red Sox-Yankees rivalry, turning it into one of the fiercest in sports.

Martinez beats Clemens in iconic duel

Two of the most esteemed pitchers in MLB history faced off on May 28, 2000. In Boston and New York’s first series of the season, they split the first two games, allowing a match-up between two of the best pitchers in the game. Boston’s Pedro Martinez was only a season removed from a 17-strikeout performance against the Yankees, an outing that raised the stakes every time he faced New York. Opposing pitcher Roger Clemens had kicked the season off on rocky footing, but had a chance to turn things around at home in the most important game of the year so far. 

Both men delivered in a big way. Martinez allowed just four hits (three were to shortstop Derek Jeter) on his way to a complete-game shutout. Clemens kept his team in the game with a big effort of his own, surrendering only two runs over nine innings. It was a home run from Boston right fielder Trot Nixon, and two runs that would end up being the difference in a fantastic pitching matchup.

Bucky Dent breaks Boston’s heart

The 1978 season saw a razor-thin race between the Red Sox and the Yankees for the AL East title. It was so close that a tiebreaker game had to be played for the fate of the division. Boston got off to a strong start with a solo home run from left fielder Carl Yastrzemski in the second inning. This gave them an advantage that doubled when right fielder Jim Rice knocked in another run with a single in the sixth. 

A 2-0 deficit heading into the seventh inning had Yankee fans contemplating a September without baseball, at least until shortstop Bucky Dent came to the plate with two men on in the top of the seventh. Dent was not known for his power, but he rocketed a three-run shot over the Green Monster to give New York a one-run lead. Another insurance run in the frame and one more in the eighth allowed the Yankees to hold on to claim the AL East.

Aaron Boone’s heroics

There is nothing like a playoff game to enhance a rivalry.  This was evident in the meeting between these teams in the 2003 ALCS. As the American League’s lone Wild Card team, the Red Sox opened the series on the road. The teams split the first two games before the Yankees took two of three in Fenway Park. Down 3-2, the Sox staved off elimination at Yankee Stadium in Game 6, forcing decisive Game 7.

Just like in the 1978 tiebreaker game, Boston started off strong. By the fourth inning, the Red Sox were up by four, but two home runs by Yankees designated hitter Jason Giambi in the fifth and seventh innings pulled New York back into striking distance. A solo shot from Giambi’s counterpart, David Ortiz, extended Boston’s lead, but it was promptly shattered by a three-run bottom-of-the-eighth hit from the Yankees.

With neither team able to score the winning run, things dragged on into the bottom of the 11th inning, when backup third baseman Aaron Boone, who had come into the game as a pinch-runner, came to the plate. He proceeded to hit a walk-off homer, sending the Yankees to the World Series and the Red Sox to the couch.

Ezra Shaw/Getty ImagesThe Red Sox’ historic ALCS comeback

A year after defeating the Sox in the ALCS in 2003, a rematch was on the table. And the stage was set even further in the offseason, when the Yankees beat out the Red Sox for an Alex Rodriguez trade. “A-Rod” later would spark a famous brawl when he scuffled with Red Sox catcher Jason Varitek in a July 24, 2004 game that would prove seminal in the rivalry.

Fast forward to October, and 2004 ALCS initially looked to be going the Yankees’ way when New York jumped to a 3-0 lead, including a 19-8  blowout in Game 3 that made it look like an easy defeat. No team had ever come back from a 3-0 deficit.

The series began to turn in favor of the Sox at Fenway Park when they beat New York in a 12-inning game, winning 6-4. Home field advantage continued in Game 5, when Boston once again managed a 5-4 victory, but this time in just nine innings. The city started to believe once again, a belief that reached a fever pitch after a 4-2 win by the Sox in Game 6. 

The final matchup was in New York, but it did not matter. Momentum had swung to the Red Sox, who were on the brink of making baseball history. A 10-3 win completed the only 3-0 comeback in MLB playoff history, sending Boston to the World Series while handing their rivals a historically painful defeat.

The ‘Curse of the Bambino’

The most iconic moment between the Yankees and the Sox occurred off the field. Two-way phenom Babe Ruth had defined Boston baseball for five years, but owner Harry Frazee made the shocking decision to sell him to the Yankees for an infusion of cash. The rest is history, with Ruth becoming baseball’s defining figure in a New York uniform as the Sox endured decades of frustration. Frazee’s decision laid the foundation for the rivalry between the two teams while helping to create a legend. 

A rivalry revived

In recent years, both teams have seen their fair share of success. The Yankees made the World Series in 2024, while the Red Sox managed to capture two titles in the 2010s. With both franchises continuing on the winning track, more additions to this rivalry list are sure to emerge.