5 Moments That Define the Red Sox-Yankees Rivalry
The intense rivalry between the New York Yankees and Boston Red Sox is well documented, and continually ranked as one of the fiercest in all of professional sports. It's perhaps only outmatched by FC Barcelona vs. Real Madrid, Ohio State vs. Michigan, or Packers vs. Bears.
The Red Sox's rivals in the Bronx have gotten the last laugh in the latest installments of the rivalry, with Walpole, Massachusetts, native Cam Schlittler ending Boston's season in Game 3 of the American League wild card round in 2025.
The series has always been back and forth; the Red Sox claimed an advantage in the 2010s and early 2020s after defeating the Yankees in the 2018 ALDS en route to their ninth World Series title and taking down the Yankees in the one-game 2021 wild card at Fenway.
Here are the five defining moments in the history of this rivalry, which has often boiled over in exceedingly entertaining fashion.
5. Bucky Dent's Home Run (1978)
Legendary Yankees shortstop Russell Earl Dent is not known in Boston as anything other than "Bucky F-ing Dent" due to the utter magnitude of his swing against Boston in the AL East tiebreaker game at Fenway on October 2, 1978.
Dent, who only hit 40 home runs in his entire 12-year career and had not built a reputation as a power hitter, came up as the go-ahead run with the Yankees trailing 2-0 in the seventh inning.
Dent's swing would change not only the trajectory of the Yankees' season but his career as well. Dent would hit his fifth home run of the season over the Green Monster to give the Yankees a 3-2 lead, a lead they would keep for the rest of the game, winning 5-4.
The Yankees, with Dent's swing, would become one of four teams to make the playoffs and earn an automatic berth to play the Kansas City Royals in the ALCS, while the Red Sox, despite having an identical 99-63 record to the Yankees entering the game, would miss the playoffs entirely.
The Yankees would steamroll the Royals and take down the Dodgers in six games, winning their 22nd World Series title and second consecutive.
4. The Pedro Martinez and Don Zimmer Fight
Ask most Red Sox or Yankees fans who have been around the block, and they'll fondly recall some of the times when tensions completely boiled over. The 2000s were filled with utter carnage between these two teams, who were each contenders at the same time, loaded with larger-than-life personas like Mariano Rivera, Alex Rodriguez, Pedro Martinez, and David Ortiz.
This won't be the only mention of the 2003 ALCS between the Yankees and Red Sox, and the next mention shouldn't be a surprise to most fans.
A brawl ensued during Game 3 at Fenway after Yankees ace Roger Clemens stoked frustration among Red Sox players by throwing pitches near them. Martinez, the ace of the Red Sox, responded by throwing a pitch over the head of outfielder Karim Garcia.
The pitch ignited a full benches-clearing brawl, and in the midst of all of it, 72-year-old Yankees bench coach Don Zimmer charged at Martinez, who sidestepped the charge and threw Zimmer to the ground.
While both Martinez and Zimmer later expressed remorse for their roles in the altercation - Martinez would later call it the biggest regret of his career - the brawl was the most infamous moment in the history of the storied rivalry and the boiling point of decades of tension between the two sides.
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3. Aaron Boone's Walk Off
The 2003 ALCS was quite possibly one of the most theatrical series in not only Yankees-Red Sox history but MLB history as a whole.
Game 7 gave the 56,279 fans at Yankee Stadium all they had asked for. The Sox struck first, with a two-run home run by Trot Nixon and solo shot by Kevin Millar punctuating a 4-0 lead by the end of four innings, and Martinez looking indomitable through seven innings.
After Mike Mussina (who entered in the fourth inning) and Rivera (who entered in the eighth) kept the Yankees in the game, the lineup finally fought back against Martinez, who controversially remained in the game for the eighth inning with the Sox up 5-2.
The move was so controversial, in fact, that one Red Sox fan and poet wrote a poem bemoaning Red Sox manager Grady Little's decision to keep Martinez in for the eighth.
The game remained tied at five until the 11th inning, when Aaron Boone stepped up to the plate against Red Sox knuckleballer Tim Wakefield. He hit the first pitch he saw into the left field seats to send the Yankees to their 39th World Series in franchise history and extend the traumatic World Series drought for their bitter rivals by one more year.
2. Boston's 2004 ALCS Comeback
Coming off the bitter 2003 ALCS loss to the Yankees, the Red Sox weren't about to let their biggest rivals get the best of them once more.
With Boston's World Series drought approaching 86 years, the story felt like a broken record as the Yankees trounced the Sox in the first three games of the ALCS, going up 3-0 after Game 1 brilliance by Mike Mussina and the Yankees' 22 hits in a 19-8 Game 3 drubbing at Fenway.
Game 4 saw the Red Sox fight back, though only after an iconic moment in which Alex Rodriguez hit a home run over the Green Monster and onto Lansdowne Street, where sour fans threw the ball back into the outfield over the 37-foot behemoth, only for the ball to be thrown back and forth over the wall until being pocketed by umpire Joe West.
The turning point in the game, and the series, was when pinch-runner Dave Roberts stole second base against Rivera, who needed just three outs to send the Yankees to the World Series once again; Roberts would score on Bill Mueller's single and tie the game. David Ortiz's walk-off home run in the 12th would force the series to a Game 5.
The Sox would not look back from there, forcing Game 5 to go to 14 innings before Ortiz's RBI single improbably sent the series back to New York, with the Red Sox down 3-2.
The Sox would handle business in New York, as Curt Schilling pitched brilliantly in the Red Sox's 4-2 win in Game 6. Schilling performed despite fighting through a torn tendon sheath in his ankle, leaving his sock bloody in an all-time rivalry moment.
Game 7 was not particularly close, as the Sox got off to a 6-0 lead after two innings and held on for a 10-3 win. The Sox would take down the St. Louis Cardinals in the 2004 World Series and break an 86-year World Series drought, and the 2004 ALCS is widely credited as the moment the tides turned for Boston.
1. Babe Ruth's Sale
While all of the previous four moments were tense and raw in their own rights, none of them would be half as intense if not for the "Curse of the Bambino," which began with the sale of two-way player Babe Ruth to the Yankees by Harry Frazee.
Frazee, who needed money to help finance the club after money woes caused by his struggling theatrical productions in New York in conjunction with dropping wartime attendance in Boston, agreed to a private deal with Yankees owners Jacob Ruppert and Tillinghast Huston to send Ruth to the Yankees for $100,000, including $25,000 cash upfront, and later, a $300,000 loan from Ruppert and a coinciding mortgage on Fenway Park.
The deal was only made necessary in 1919, when Ruth, then a rising star with the Red Sox, demanded money only paid to star Ty Cobb. Ruth got his way, being paid $10,000 for the 1919 season, but after he broke a record with 29 home runs in 1919, it was clear the Sox couldn't meet his demands for a new contract worth $20,000.
After Ruth was sold to the Yankees, the fates of the two teams couldn't have possibly been further apart. The Yankees would become a full-blooded dynasty in the 1920s, and the Red Sox would go 86 years without a title as their rivals became baseball's most storied franchise.
In the backdrop of Bucky Dent, Pedro Martinez, Aaron Boone, and David Ortiz was the Curse of the Bambino, and the sale of Ruth will always go down as the most infamous moment in the history of the rivalry.
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This story was originally published June 9, 2026 at 2:08 PM.