Red Sox vs New York Yankees Timeline: Key Moments

In this article

• The First Meetings: 1903–1919
• The Sale That Changed Baseball: Babe Ruth and the Curse
• The Long Drought: The Yankees Dynasty Years
• 1949: The Pennant Decided on the Final Weekend
• 1978: The Bucky Dent Game
• 1986: One Strike Away
• 1999: The First October Meeting
• 2003: Aaron Boone and the Boonebino
• 2004: The Greatest Comeback in Baseball
• The Modern Era: 2018, 2021 and 2025
• Red Sox vs New York Yankees Timeline at a Glance
• Frequently Asked Questions
• Conclusion

The Boston Red Sox and the New York Yankees have been playing each other for more than 120 years, and no rivalry in American sports carries quite the same weight. It began on May 7, 1903, when the Boston Americans beat the New York Highlanders 6-2 at the Huntington Avenue Grounds, and it has been running ever since. What makes this red sox vs new york yankees timeline so gripping is not just the length of it, but the shape of it: Boston dominated first, then sold its biggest star to New York, then spent 86 years paying for it, then produced the greatest comeback in baseball history to end the drought.

For fans, the rivalry is a living history. Every generation has its own defining moment. Older fans talk about 1949 and 1978. A middle generation remembers 1986 and the ball that went through Bill Buckner’s legs. Younger fans grew up on Aaron Boone’s walk-off home run in 2003 and the impossible comeback of 2004. This timeline walks through those moments in order, with the dates and scores that actually happened, so you can see how one of sport’s great feuds was built, game by game.

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The First Meetings: 1903–1919

When the two clubs first met, neither was called by the name fans know today. Boston played as the Americans, and New York played as the Highlanders. Both were part of the young American League, and the early years belonged firmly to Boston. The Americans won the first World Series ever played, in 1903, and by the time the decade turned, Boston had become the most successful franchise in the young sport.

The Red Sox won five of the first fifteen World Series: 1903, 1912, 1915, 1916 and 1918. No other team had that many titles at the time. The Yankees, meanwhile, were still finding their feet. They shared the Polo Grounds with the New York Giants and had no local American League rival of their own. They had never won a pennant, let alone a World Series, and for the first two decades of the rivalry they were very much the junior partner.

The teams even decided a pennant against each other in the final series of the 1904 season, with Boston coming out on top. It was an early sign of what this fixture would become: the two clubs seemed drawn to each other at the moments that mattered most. But nobody in 1904 could have guessed how dramatically the balance of power was about to flip.

One of Boston’s stars during this golden run was a young left-handed pitcher named Babe Ruth. He helped the Red Sox win three of those championships, in 1915, 1916 and 1918, and by 1919 he was changing the game itself. That season he hit 29 home runs, the most any player had ever hit in a single season. He wanted to play every day, not just pitch, and his bat was becoming the most feared weapon in baseball. He was, in every sense, the biggest star in the sport. And Boston was about to sell him.

The Sale That Changed Baseball: Babe Ruth and the Curse

In the winter of 1919–20, Red Sox owner Harry Frazee sold Babe Ruth’s contract to the New York Yankees in a straight cash deal. The sale was agreed in late December 1919 and completed on January 3, 1920. Frazee, a theatre producer who was often short of cash to finance his stage projects, needed the money. The Yankees’ owner, Jake Ruppert, announced the purchase at a morning press conference, telling reporters the club had bought Ruth for a six-figure sum with no players involved.

The effect was immediate and total. Ruth hit 54 home runs in his first season in New York, a number that seemed impossible in an era just emerging from the dead-ball years. The Yankees won their first American League pennant in 1921 and their first World Series in 1923. Within a few years they had moved out of the Polo Grounds and into their own home in the Bronx, Yankee Stadium, a ballpark that became known as the House That Ruth Built. Ruth’s lineup became famous as Murderers’ Row, and the Yankees reached the World Series seven times during his years in New York, winning four of them.

Boston, meanwhile, collapsed. The Ruth deal was not the only sale Frazee made to the Yankees, and the club finished last nine times in the eighteen seasons that followed. The Red Sox would not win another World Series for 86 years. Fans eventually gave the drought a name: the Curse of the Bambino. The phrase did not become widely used until Boston Globe columnist Dan Shaughnessy published a book of that title in 1990, but once it caught on, it framed everything that followed. Every Boston failure, no matter how it happened, was read as another chapter of the curse.

The Long Drought: The Yankees Dynasty Years

For most of the middle of the twentieth century, the rivalry was painfully one-sided. The Yankees became the greatest dynasty in baseball, collecting pennants and championships at a pace no other franchise could match. The Red Sox had fine players and fine teams, but they kept coming up short, and the shortfalls kept happening in the cruellest ways.

Boston came close to a World Series title in 1946, 1967 and 1975, but lost each time. The 1975 team in particular captured the imagination, taking the Cincinnati Reds to seven games in a classic World Series, but it still ended in defeat. By then the curse had become part of the club’s identity, a story Boston fans told with a mixture of pride and dread. The Yankees, for their part, barely needed to mention it. The standings did the talking.

Yet the rivalry never went quiet, because the two teams kept meeting in races that went down to the final days of the season. The 1949 pennant race was the first great example of that, and it set a pattern that would repeat for decades: Boston and New York, tied or nearly tied, with everything on the line in the last series of the year.

1949: The Pennant Decided on the Final Weekend

The 1949 season was Casey Stengel’s first as Yankees manager, and it was a year defined by injuries. Joe DiMaggio, the Yankees’ star centre fielder, missed the first 65 games with a bone spur in his heel and did not make his season debut until June 28, at Fenway Park. He answered the wait in style, homering in his second at-bat, hitting two more the next day, and helping the Yankees sweep the three-game series in Boston. He finished the shortened season batting .346 with 14 home runs in 76 games.

The Red Sox, managed by former Yankees skipper Joe McCarthy and led by Ted Williams, stayed close all year. Williams put together a near-Triple Crown season, leading the league with 43 home runs and 159 runs batted in. Late in September, Boston swept the Yankees in a three-game series to take first place, and the race came down to a final two-game series at Yankee Stadium on October 1 and 2. Boston needed to win just one of the two games to clinch the pennant.

The Yankees won them both. The first game finished 5-4, with DiMaggio back in the lineup after missing time with pneumonia. The second finished 5-3, with Vic Raschi shutting Boston out on two hits through eight innings. The Yankees took the pennant by a single game, then beat the Brooklyn Dodgers in five games to win the World Series. It was the first of five straight championships for Stengel’s Yankees, and for Boston it was another near miss to add to the list.

1978: The Bucky Dent Game

If 1949 was painful for Boston, 1978 was worse, because the Red Sox had the division in their hands and let it slip away. Boston led the American League East by as many as 14 games during the summer, but the Yankees clawed back, and the two teams finished the regular season tied with identical 99-63 records. That forced a one-game playoff at Fenway Park on October 2, 1978, to decide the division title.

Boston led 2-0 going into the seventh inning behind starter Mike Torrez, and Fenway was ready to celebrate. Then, with two men on base and one out, light-hitting Yankees shortstop Bucky Dent lifted a fly ball toward the Green Monster. Dent had fouled a ball off his foot earlier in the at-bat and was swinging a borrowed bat, handed to him by teammate Mickey Rivers after his own bat cracked. The ball cleared the wall for a three-run home run, his fifth of the season, and the Yankees led 3-2.

New York added two more runs and held on to win 5-4, completing a comeback from 14 games back that still stands as one of the great collapses in baseball history. The Yankees went on to win the World Series, with Dent named the Most Valuable Player of the Fall Classic after hitting .417. In Boston, the game became known simply as the Bucky Dent Game, and Dent’s name became a byword for heartbreak in New England.

1986: One Strike Away

By 1986 the curse had become the story of the rivalry, and that October it produced its most famous scene. The Red Sox were not even playing the Yankees that autumn. They were in the World Series against the New York Mets, leading the series three games to two and leading Game 6 by 5-3 in the bottom of the tenth inning at Shea Stadium on October 25, 1986.

Boston was one strike away from its first championship since 1918, twice over, with two outs and nobody on base. Then Gary Carter, Kevin Mitchell and Ray Knight singled in succession, and a wild pitch by Bob Stanley tied the game at 5-5. Mookie Wilson came to the plate and hit a slow ground ball toward first base. Bill Buckner, playing on badly damaged ankles, bent down to field it, and the ball rolled between his legs into right field. Knight raced home from second, and the Mets won 6-5 in ten innings.

Two nights later the Mets won Game 7, 8-5, and the championship was gone again. Buckner’s error did not lose the series on its own. The game was already tied when the ball went through his legs, and Boston still had a seventh game to play. But the image of the ball trickling past him became the defining picture of the curse, and it is still shown every October. For Red Sox fans it was proof, if any were needed, that the Bambino was still at work.

1999: The First October Meeting

For all their history, the Red Sox and Yankees had never met in the postseason until 1999. The expanded playoff format finally brought them together, and the first meeting went the way most of the rivalry had gone. The Yankees won the American League Championship Series four games to one, and then swept the Atlanta Braves to win the World Series.

Boston’s only win in the series was a memorable one: a 13-1 rout in Game 3 behind Pedro Martinez, pitching against former Red Sox ace Roger Clemens, who had joined the Yankees that season after thirteen years in Boston. It was a small consolation, but it hinted at what was coming. The two clubs were now meeting in October, and the stakes were only going to get higher.

2003: Aaron Boone and the Boonebino

Four years later, the rivalry produced its most dramatic chapter yet. The 2003 American League Championship Series went to a deciding seventh game at Yankee Stadium on October 16, 2003, and Boston had it in their grasp. The Red Sox led 5-2 going into the bottom of the eighth inning, five outs away from the pennant.

Then came the decision that Boston fans still argue about. Manager Grady Little left a tiring Pedro Martinez in the game, and the Yankees tied it at 5-5. The game went to extra innings, with Mariano Rivera shutting Boston down and Tim Wakefield doing the same for the Red Sox through the tenth. In the bottom of the eleventh, Aaron Boone, who had entered the game as a pinch runner in the eighth and had not yet had a plate appearance, led off against Wakefield. He hit the first pitch he saw into the left-field stands for a walk-off home run, and the Yankees won 6-5.

The game had started on the evening of October 16 and finished after midnight on October 17. Newspapers dubbed the moment the Curse of the Boonebino. The Yankees went on to lose the World Series to the Florida Marlins, but that was no comfort in Boston. The Red Sox had been five outs from ending 85 years of hurt, and they had lost. It felt, at the time, like the curse would never end.

2004: The Greatest Comeback in Baseball

One year later, it did. The 2004 American League Championship Series is the centrepiece of this red sox vs new york yankees timeline, and it remains the only time a Major League Baseball team has come back from a 3-0 deficit to win a best-of-seven series. The series ran from October 12 to October 20, and for the first three games it looked like a repeat of 2003, only worse.

The Yankees won Game 1 in the Bronx, then Game 2, and then humiliated Boston 19-8 in Game 3 at Fenway Park. No team in baseball history had ever recovered from 3-0 down. The Boston Globe’s headline the next day asked: “How much more can New Englanders take?” The answer, it turned out, was: not much more, because the comeback started that very night.

Game 4 is the most famous game in the series. The Yankees led 4-3 in the bottom of the ninth inning at Fenway, with Mariano Rivera, the greatest closer in the game’s history, on the mound. Kevin Millar walked, Dave Roberts came in to pinch run, and Roberts stole second base. Bill Mueller singled him home to tie the game, and in the bottom of the twelfth inning David Ortiz hit a walk-off home run into the right-field bleachers. Boston was alive.

Game 5 went even longer. The Red Sox came from behind again in the eighth inning, and Ortiz delivered another walk-off, a single in the bottom of the fourteenth inning that scored Johnny Damon. The game ended less than twenty-three hours after Game 4 had finished. Boston had won two straight extra-inning games, and the series was going back to New York.

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In Game 6, Curt Schilling pitched seven strong innings on an injured ankle, allowing just one run, and Boston won to force a seventh game. Game 7 was barely a contest. Ortiz homered in the first inning, Damon hit two home runs including a grand slam in the second, and the Red Sox won 10-3 at Yankee Stadium. Four straight wins, after three straight losses, against the team that had tormented them for 86 years.

Eight days later, Boston swept the St. Louis Cardinals in the World Series to win its first championship since 1918. The Curse of the Bambino was over, ended by the team that had supposedly created it, in the most dramatic way imaginable. The 2004 comeback is still described as the greatest comeback in sports history, and it changed the rivalry for good. Boston no longer played the Yankees as the cursed underdog. The two clubs were, at last, equals again.

The Modern Era: 2018, 2021 and 2025

The rivalry did not fade after 2004. If anything, the modern era has been more even than any period before it, with the October meetings split down the middle. Boston won the next postseason meeting in 2018, beating a 100-win Yankees team 3-1 in the American League Division Series on the way to a World Series title of their own. That series featured Brock Holt hitting the first postseason cycle in Major League Baseball history, and the Red Sox finished the season with 108 wins, the best record in franchise history.

Three years later, the clubs met in a single-elimination Wild Card game at Fenway Park. On October 5, 2021, Boston beat New York 6-2 behind home runs from Xander Bogaerts and Kyle Schwarber off Yankees ace Gerrit Cole. It was Boston’s third straight postseason series win over the Yankees, following 2004 and 2018.

The Yankees answered in the 2025 Wild Card Series, winning the best-of-three set 2-1 at Yankee Stadium. Boston won the opener, but New York took Games 2 and 3 to advance, evening the postseason series count between the clubs at three wins apiece. The rivalry that began in 1903 is still being written, and the next chapter is never far away. Every season brings another series at Fenway or in the Bronx, another chance for one side to add a moment that fans will still be talking about decades from now.

Red Sox vs New York Yankees Timeline at a Glance

Frequently Asked Questions

When did the Red Sox vs Yankees rivalry start?

The rivalry started on May 7, 1903, when the Boston Americans beat the New York Highlanders 6-2 at the Huntington Avenue Grounds in Boston. Both teams were in their first season in the American League, and they have played each other every year since.

What is the Curse of the Bambino?

The Curse of the Bambino is the superstition that the Boston Red Sox were cursed after selling Babe Ruth to the New York Yankees in the winter of 1919–20. Boston had won five World Series before the sale and did not win another for 86 years, until 2004. The phrase became famous after Dan Shaughnessy’s book of the same name was published in 1990.

What happened in the 2004 ALCS?

The Red Sox lost the first three games of the 2004 American League Championship Series to the Yankees, then won four in a row to take the series 4-3. It was the first and only time a Major League Baseball team has come back from a 3-0 deficit to win a best-of-seven series. Boston then swept the St. Louis Cardinals in the World Series to end the 86-year championship drought.

Who hit the most famous home runs in the rivalry?

Three home runs stand above the rest. Bucky Dent’s three-run shot in the 1978 one-game playoff gave the Yankees a 5-4 win at Fenway Park. Aaron Boone’s walk-off home run in the eleventh inning of Game 7 of the 2003 ALCS won the pennant for New York. And David Ortiz’s walk-off home run in the twelfth inning of Game 4 of the 2004 ALCS kept Boston alive and started the greatest comeback in baseball history.

Who has won more postseason series between the Red Sox and Yankees?

The postseason meetings are tied at three series wins each. The Yankees won the 1999 and 2003 ALCS and the 2025 Wild Card Series, while the Red Sox won the 2004 ALCS, the 2018 ALDS and the 2021 Wild Card game. Across those six series, the games are split almost evenly as well, which is why this rivalry is still argued about every October.

Conclusion

The red sox vs new york yankees timeline is more than a list of games. It is the story of how a rivalry was built: first by Boston’s early dominance, then by the most famous sale in sports history, then by 86 years of heartbreak, and finally by a comeback that no one thought was possible. The moments that define it, the Ruth sale, the 1949 pennant race, Bucky Dent, Bill Buckner, Aaron Boone and the 2004 comeback, are not just baseball history. They are the shared memory of two cities and two sets of fans who have spent more than a century measuring themselves against each other.

What comes next is unwritten, but the pattern of this rivalry suggests it will be dramatic. The modern era has been the most even yet, with the postseason meetings tied at three series apiece and every October meeting going down to the wire. The next great moment in the Red Sox vs Yankees timeline is probably only a season away, and when it happens, fans on both sides will know exactly where they were when they saw it.

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