Yankees–Red Sox Rivalry

The Yankees–Red Sox rivalry is a Major League Baseball (MLB) rivalry between the New York Yankees and the Boston Red Sox. Both teams have competed in MLB's American League (AL) for over 120 seasons and have since developed what is arguably the fiercest rivalry in all of American sports. In 1919, Red Sox owner Harry Frazee sold star player Babe Ruth to the Yankees, which was followed by an 86-year period in which the Red Sox did not win a World Series. This led to the popularization of a superstition known as the " Curse of the Bambino," which was one of the most well-known aspects of the rivalry.

The rivalry is often a heated subject of conversation, especially in the home region of both teams, the Northeastern United States.
Until the 2014 season, every season's postseason had featured one or both of the AL East rivals since the inception of the wild card format and the resultant additional Division Series in 1995; they have faced each other in the AL Championship Series (ALCS) three times. The Yankees won twice, in 1999 and 2003; while the Red Sox won in 2004. The two teams have also met once in the AL Division Series (ALDS), in 2018, with Boston winning 3–1, a series which included a 16–1 Red Sox win in Game 3 at Yankee Stadium, the most lopsided postseason loss for the Yankees in their history. In addition, the teams have twice met in the last regular-season series of a season to decide the league title, in 1904 (when the Red Sox, then known as the Americans, won) and 1949 (when the Yankees won). On October 5, the Red Sox also beat the Yankees in the 2021 American League Wild Card (play-in) Game, 6-2, which was held at Fenway Park.

The Yankees and the Red Sox finished tied for first in 1978; subsequently, the Yankees won a high-profile tie-breaker game for the division title. The first-place tie came after the Red Sox had a 14-game lead over the Yankees more than halfway through the season. Similarly, in the 2004 ALCS, the Yankees ultimately lost a best-of-7 series after leading 3–0. The Red Sox comeback was the only time in American baseball history that a team has come back from a 0–3 deficit to win a series. The Red Sox went on to win the World Series, ending the 86-year-old curse.

This match-up is regarded by some sports journalists as the greatest rivalry in sports. Games between the two teams often generate considerable interest and receive extensive media coverage, including being broadcast on national television. National carriers of Major League Baseball coverage, including Fox/FS1, ESPN, and MLB Network carry most of the games in the rivalry across the nation, regardless of team standings or playoff implications. Yankees–Red Sox games are some of the most-watched MLB games each season. Outside of baseball, the rivalry has led to violence between fans, along with attention from politicians and other athletes.

Background

Boston and New York City have shared a rivalry as cities since before the American Revolution. For more than a century after its founding, Boston was arguably the educational, cultural, artistic, and economic power in the United States. Its location as a close American port to Europe and its concentration of elite schools and manufacturing hubs helped maintain this position for several decades. During this time period, New York was often looked down upon as the upstart, over-populated, dirty cousin to aristocratic and clean Boston.

In the 19th century, however, New York's economic power outpaced Boston's, fueled by possession of the terminus of the Erie Canal, which spurred massive growth in the manufacturing, shipping, insurance and financial services businesses. Another factor was its more rapid population expansion compared to that of Boston, driven by the growth of these industries, by New York's popularity as an immigration port of entry, and enhanced by a larger population base, even prior to the construction of the Canal – on the eve of the Revolution, New York, with 30,000 people, had nearly twice the population of Boston, with about 16,000. By the start of the 20th century the original dynamic, centered on Boston, had completely shifted as New York, particularly Wall Street, became the financial center of both the United States and the world.

The cities even played two different versions of early baseball. The "Massachusetts Game," as it was called, was played on a field with four bases and with home plate in the middle; whereas, the "New York Game," popularized by the New York Knickerbocker Club, was played on a diamond with three bases. The "New York Game" spread throughout the nation after the American Civil War and became the foundation for the modern game of baseball.

Red Sox' early success

The Red Sox were one of the most successful teams in baseball from 1901 to 1918. They won the inaugural World Series in (as the Boston Americans; the team changed its name to Red Sox in 1908) and four more between and . In 1901, the Yankees, then known as the Baltimore Orioles, played in Maryland for two seasons before moving north. The two teams had their first meeting in Baltimore on April 26, 1901, the inaugural year of the American League. On May 7, 1903, both teams played for the first time after the Orioles franchise was moved to New York after being purchased as a defunct team and became the New York Highlanders, in reference to playing games in the Washington Heights neighborhood of Manhattan. The game was marked by a fight when Boston pitcher George Winter was knocked down. Boston would eventually go on to win the pennant and the inaugural 1903 World Series. The 1904 season featured the teams facing each other on opening day. Later in the season, the Highlanders, led by pitcher Jack Chesbro in his record-setting 41 game-winning season, met the Boston Americans in the season's final game to decide the American League pennant winner. Chesbro threw a wild pitch in the top of the ninth inning, allowing the winning run to score from third base, and Boston won the game, and the pennant. The New York Giants, who had already clinched the National League pennant, refused to play in the 1904 World Series because of a perception of the "Junior Circuit" as being inferior (and because of alleged animosity between American League founder and first president, Ban Johnson, and the hierarchy of the Giants, owner John T. Brush and his team's Hall of Fame coach, player-manager John McGraw); thus, there was no World Series that year. Not until 2004 would the Red Sox again defeat the Yankees in a title-deciding game.

On April 11, 1912, the Highlanders debuted their pinstripes in a game against Boston, by then known as the Red Sox. Nine days later, Boston opened Fenway Park with a game against the Highlanders, who had left their home field of Hilltop Park to play in the newly-rebuilt Polo Grounds; soon thereafter, in 1913, the team dropped the nickname Highlanders in favor of Yankees.

Six years later, the Chicago Cubs scored two runs off of Babe Ruth in game 4 of the Series, snapping his then record World Series scoreless inning streak at innings. The Red Sox won the game, 3–2, and went on to capture their fifth Series title, their third in four years, and fourth in seven years.

The Yankees would however receive one notable moment of glory against the Red Sox during this era. On April 24, 1917, Yankees pitcher George Mogridge threw a no-hitter at Fenway Park, the first in the ballpark's history and first in Yankees history.

Babe Ruth sold to Yankees

In 1916, Broadway producer Harry Frazee purchased the Red Sox, on credit, for $500,000. Frazee lost his patience with Ruth despite the latter's success with the Red Sox, as Ruth had threatened to hold out for a larger contract and become a distraction. After the Red Sox finished sixth in the American League in 1919, Frazee, needing money to finance a Broadway musical, often said to be ''No, No Nanette'' (the success of that 1925 play is actually what paid off the loan). However, Ruth was sold to the Yankees in 1919, and "No, No Nanette" was produced by Frazee in 1925. Frazee received $125,000 and a loan of $300,000 — secured on Fenway Park — for Ruth, despite Ruth having set the record for home runs with 29 in 1919. This began a series of deals with the Yankees that resulted in a long period of mediocrity for the Red Sox while the Yankees began their dynasty.

Ruth's arrival in New York simultaneously launched the Yankees dynasty while ravaging the Red Sox. While the Red Sox' five World Series titles were a record at the time, 1918 would be the team's last championship for 86 years. Meanwhile, Ruth's home run-hitting prowess anchored the Yankees line-up, which became known as "Murderers' Row" in the late 1920s. The Yankees reached the World Series seven times during Ruth's New York years, winning four. This abrupt reversal of fortunes for the Red Sox marked the beginning of the supposed "Curse of the Bambino." But it was not the Ruth deal alone that reversed the fortunes of both clubs. Frazee also sold many other players to the Yankees.

Robert W. Creamer reported that " heloan was made and relations between the two clubs continued to be cordial, with Frazee sending player after player to the Yankees over the next few seasons for more and more cash. This was no accident. Frazee and Yankees owner Tillinghast L'Hommedieu Huston were friends, and American League president Ban Johnson's attempts to drive Frazee out of the game had caused the five teams loyal to Johnson to make no deals with the Red Sox as long as Frazee owned the club, leaving only the Yankees and White Sox as trading partners. When the White Sox' reputation was destroyed in the Black Sox Scandal, Frazee's only option for trades was to deal with the Yankees. The Red Sox soon became a baseball disaster area, finishing dead last nine times in eleven seasons."

Among others, Wally Schang, Everett Scott, Carl Mays, Waite Hoyt, Joe Bush and Sam Jones went from the Sox to the Yankees in the next one to three years, along with Ed Barrow, the former Red Sox manager who became the Yankees' general manager and empire-builder for the first quarter-century of the Yankees' dynasty. Scott, a former Red Sox team captain, actually took the reins as Yankees captain from Ruth when he arrived; in doing so, he became the only player in history to be named captain for both teams.

Curse of the Bambino

From 1920 through 2003, the Yankees won 26 World Series championships and 39 pennants, compared to only four pennants for the Red Sox. In every year that the Red Sox won the pennant—1946, 1967, 1975 and 1986—they lost the World Series 4–3, leaving them with no World Series titles. During this time, the Red Sox finished second in the standings to the Yankees on twelve occasions—in 1938, 1939, 1941, 1942, 1949, 1977, 1978, and every year from 1998 to 2003. During the 84-year period, the Yankees finished with a better regular-season record than the Red Sox 66 times, leading one sportswriter to quip that the Yankees' rivalry with the Red Sox was much like the rivalry "between a hammer and a nail." The Yankees finished second in the standings to the Red Sox twice, in 1986 and 1995.

1920s and 1930s: First Yankees dynasty

Just two years after Ruth's sale, he went on to have a record setting season, one of the greatest in major league history for a batter. This propelled the Yankees to win their first pennant and face their cross-town rival. Ruth got hurt during the Series, and the Yankees eventually dropped the last three games, losing the Series 5–3 to the Giants in the last ever best-of-nine Series. Both the Yankees and Giants would play in the 1922 World Series as well, a series that would be the Yankees' last in the two teams' shared stadium at the Polo Grounds, as the Giants served the Yankees an eviction notice after the 1921 season.

The Yankees moved across the Harlem River to the Bronx into Yankee Stadium. On April 18, 1923, the Yankees opened their new home against the Red Sox. Over 74,200 people watched the Yankees defeat the Red Sox, 4–1, in the first game played at the stadium. Babe Ruth hit the new stadium's first home run, christening the stadium as "The House that Ruth Built." Ruth would finish the year with a .393 batting average and the Yankees won their first World Series that year. Of the 24 players on the Yankees, 11 previously played for the Red Sox.

Several lesser known moments in the rivalry occurred during the 1930s. Pitcher Red Ruffing was traded in 1930 from the Red Sox to the Yankees. Ruffing, who had limited success with the Red Sox, would go on to a Hall of Fame career with the Yankees winning six World Series. On May 30, 1938, before 83,533 spectators at Yankee Stadium, Yankees outfielder Jake Powell and Red Sox player-manager Joe Cronin fought on the field and beneath the stands. Both players were fined and suspended for 10 games. The Yankees and Red Sox would finish first and second in the League respectively that year as well as the following. The Yankees went on to sweep the Chicago Cubs in the World Series and the Cincinnati Reds in the World Series a year later.

1940s–1960s: Teddy Ballgame, Joltin' Joe the Yankee Clipper

The rivalry intensified in 1941 when Ted Williams of the Red Sox batted .406, becoming the last player to bat over .400 in a season. Despite his accomplishment, Williams lost the AL MVP race to the Yankees' Joe DiMaggio, who in the same season set the record for a hitting streak, with 56 straight games with a hit. Williams later reminisced about his rivalry with DiMaggio saying "DiMaggio was the greatest all-around player I ever saw. His career cannot be summed up in numbers and awards. It might sound corny, but he had a profound and lasting impact on the country." Both teams almost swapped the two players. In 1947, Boston Red Sox owner Tom Yawkey and Yankees GM Larry MacPhail were rumored to have verbally agreed to trade DiMaggio for Williams, but MacPhail refused to include Yogi Berra and the deal fell through. Joe DiMaggio's younger brother Dom would play for the Red Sox his entire career during the 1940s.

The Red Sox won 15 games in a row in 1946. They were unstoppable and were in first place all but two days in the season, and would play in their first World Series game since 1918, having finished ahead of the Yankees in the American League for the first time since selling Babe Ruth. Since the Red Sox last pennant in 1918, the Yankees had won 14 pennants and 10 World Series. Boston would eventually lose the Series 4–3 to the St. Louis Cardinals.

Former Yankees manager Joe McCarthy came out of retirement after a feud with Yankees ownership to sign with the Red Sox as their manager in 1948. Both the Yankees and the Red Sox were involved in a tight pennant race with the Cleveland Indians until the final weekend. The Red Sox eliminated the Yankees in the final series at Fenway Park, overcoming four DiMaggio hits in the final game to tie Cleveland for the pennant. The situation forced the first-ever one-game playoff in AL history, which the Indians won 8–3 at Fenway Park and preventing the first all-Boston World Series, as the Indians went on to defeat the Boston Braves in the Series.

A year later, the Red Sox entered the final series of the season at Yankee Stadium needing only one win over the Yankees to advance to the World Series. The Sox lost 5–3 on the last day of the season after falling 5–4 the previous day, resulting in the Yankees winning the AL pennant. The Yankees went on to defeat the Brooklyn Dodgers in the 1949 World Series for their 12th championship.

The 1951 season opened up at Yankee Stadium. The Yankees defeated the Red Sox in public address (PA) announcer Bob Sheppard first game. Sheppard would go on to serve PA duties at Yankee Stadium for another 56 years. On September 28 of that year, Yankees pitcher Allie Reynolds pitched a no-hitter against the Red Sox. A year later, Red Sox outfielder Jimmy Piersall and Yankees second baseman Billy Martin exchanged insults before a game in Boston, and ended up fighting in the tunnel under the stands. The fight was eventually broken up by Yankees coaches Bill Dickey and Oscar Melillo, and Boston starting pitcher Ellis Kinder. Piersall changed out of his bloody shirt and promptly fought with teammate Maury McDermott. The Red Sox won 5–2 with Piersall sitting the game out.

The Yankees won five consecutive World Series titles from 1949 to 1953, breaking their previous streak of four straight titles from 1936 to 1939. They would also go on to win 14 AL pennants in 16 years from 1949–1964.

1961–1980: Milestones, fights, close finishes, and the Bucky Dent game

The 1961 season saw the chase of Babe Ruth's 1927 single season home run record by Roger Maris and Mickey Mantle. Both Maris and Mantle would continue to reach the home run record until Mantle got injured late in the season, leaving Maris to reach the record. On the last day of the season, Maris broke the record with his 61st home run of the year off Red Sox pitcher Tracy Stallard at Yankee Stadium. Former Hall of Fame shortstop for the Yankees, Phil Rizzuto, called the shot in what was one of his first games as an announcer. The Yankees won the game 1–0 to win their 26th American League pennant and then to win their 19th World Series title.

The next year, the Red Sox had been in the middle of a streak of eight straight losing seasons. The team was so bad, that after a 13–3 loss to the Yankees on July 26, Red Sox ace Gene Conley got off the bus and attempted to leave the country and go to Israel. Conley was denied his request because he did not have a passport. Nonetheless, Conley stayed away from the team for three days.

In 1967, Red Sox pitcher Billy Rohr came within a single strike of a no-hitter at Yankee Stadium. Elston Howard hit a two-out, two-strike single in the ninth to break the no-hit bid. Rohr completed the one-hitter, but ultimately finished his career with only two wins, both coming against the Yankees. Later that year, Red Sox third baseman Joe Foy hit a grand slam during the first game of a two-game series. In the second game, Yankees pitcher Thad Tillotson threw two brushback pitches at Foy before beaning him in the batting helmet. In the next inning, Red Sox pitcher Jim Lonborg beaned Tillotson. Both pitchers yelled at each other, and then a brawl ensued. During the fight, Red Sox outfielder Reggie Smith picked up and body-slammed Tillotson to the ground. Two months later, both teams were involved in the longest game ever played (by innings) at Yankee Stadium. New York recorded a 20-inning 4–3 victory over Boston. Earlier that year on August 3, the Yankees traded Howard to the Red Sox to help bolster their team during the pennant race. When Howard returned to Yankee Stadium in a Red Sox uniform, the Yankees fans gave him a standing ovation. Boston would be led by Hall of Famer Carl Yastrzemski's historic season winning the batting triple crown, leading the Red Sox to the pennant in what was a dream year for the Sox. Howard's contribution would be instrumental in the 1967 World Series, but he and Yastrzemski would lose to Bob Gibson and the St. Louis Cardinals four games to three.

In 1973, the American League adopted the designated hitter rule. On April 6, opening the season at Fenway Park, Ron Blomberg of the Yankees became the first designated hitter in Major League history. Red Sox pitcher Luis Tiant walked Blomberg in his first plate appearance of the game. Later that year at Fenway Park, with the score tied 2–2 in the top of the ninth, Yankees catcher Thurman Munson attempted to score from third base on a missed bunt by Gene Michael. He crashed into Red Sox catcher Carlton Fisk resulting in a fight with Munson punching Fisk in the face. The rivalry intensified in the 1970s with the fans too, as just a year later in 1974 at Fenway Park, Yankees first baseman Chris Chambliss was struck in the right arm with a dart thrown from the stands after hitting an RBI ground-rule double. Two years later, Yankees outfielder Lou Piniella would crash into Fisk feet first in an attempt to score in the sixth inning of a game at Yankee Stadium. The two benches cleared while Piniella and Fisk brawled at home plate. After the fight apparently died down and order appeared to be restored, Sox pitcher Bill Lee and Yankees third baseman Graig Nettles and center fielder Mickey Rivers began to exchange words, resulting in another fight. Lee suffered a separated left shoulder from the tilt and missed the next 51 games of the 1976 season. He would continue to pitch until 1982. The 1976 season saw the Yankees win the pennant, but lose to the Big Red Machine in the 1976 World Series, just like the Red Sox had done a year prior in the 1975 World Series in which Carlton Fisk hit his famous home run off of the left field foul pole at Fenway Park.

After the Yankees' loss to the Reds, owner George Steinbrenner committed to sign marquee free agent Reggie Jackson to help win a championship. The Yankees, Red Sox, and Baltimore Orioles would battle each other the entire year in the division race. The Yankees would win the division for the second year in a row, while the Orioles and Red Sox finished tied for second, games behind the Yankees. Jackson's entry onto the Yankees initially had caused a lot of friction on them. In the middle game of what would prove to be a three-game series sweep by the Red Sox at Fenway Park, Yankees manager Billy Martin pulled Reggie Jackson off the field in mid-inning for failing to hustle on a ball hit to the outfield. The extremely angry and highly animated Martin had to be restrained by coaches Yogi Berra and Elston Howard from getting into a fistfight with Jackson in the dugout during the nationally televised game. Eventually, emotions calmed down for the season and the Yankees came together to recapture the pennant and defeat the Los Angeles Dodgers in the 1977 World Series, their first since .

In 1978, the Red Sox, led by Jim Rice, Carl Yastrzemski, Fred Lynn and catcher Carlton Fisk, and managed by future Yankees coach Don Zimmer, were looking good for the World Series for the second time in the decade. They led the Yankees in the standings by 14 games in mid-July, with less than three months to go in the regular season. The Yankees turned their season around just as the Red Sox started to collapse. By September 7, the Yankees had whittled down the 14-game deficit to only four games, just in time for a four-game series at Fenway Park in Boston. The Yankees won all four games in the series by a combined score of 42–9. This series became known as the "Boston Massacre". On September 16, the Yankees held a -game lead over the Red Sox, but the Sox won 12 of their next 14 games to overcome that deficit and finish in a first-place tie with the Yankees. A tie-breaker game was scheduled in Boston to determine who would win the AL East pennant for 1978.

Boston pitted former Yankees pitcher Mike Torrez against the Yankees' Cy Young Award winner, Ron Guidry, who took a 24–3 record into the game. The Sox were beating Guidry 2–0 in the top of the seventh inning when light-hitting Yankees shortstop Bucky Dent hit a two-out, three-run home run over Fenway Park's Green Monster to take a 3–2 lead. It was only his fifth home run of the season. The Yankees later led 5–2 and held on to win 5–4 when Yastrzemski popped out with runners on first and third, ending the Red Sox' season. Yankees closer Goose Gossage notched his 27th save of the season. Gossage would later comment years later about how he was spat on at Fenway Park and had beer thrown in his face. "There is no rivalry in sports that rivals the Yankees—Red Sox...that playoff game in '78–it felt like the playoffs and World Series were exhibition games after that." The headline in ''The Boston Globe'' the next day summed it all up: "Destiny 5, Red Sox 4." New York went on to defeat the Kansas City Royals in the ALCS and the Los Angeles Dodgers in the World Series for their second straight championship.

1980s and early 1990s

1980s: No championships

The 1980s is the only decade in which neither the Yankees nor the Red Sox won a World Series. Although both teams went to a World Series during that decade, the Red Sox were not serious contenders in the Yankees' playoff years (1980 and 1981), but the Yankees seriously contended in the Red Sox' playoff years (1986 and 1988).

The Yankees lost the World Series in , while the Red Sox loss came in 1986. Both times, the teams lost after being up 2–0 in their respective World Series. For the Yankees, the loss in 1981 marked the beginning of the team's demise and downfall in the 1980s and early 1990s. Despite the lack of championships, the rivalry between the teams did have some memorable highlights. Yankees left-hander Dave Righetti threw a no-hitter against the Red Sox at Yankee Stadium. One of the game's greatest hitters, Wade Boggs, struck out to end the game.

On October 4, 1986, Righetti once again made history against the Red Sox when he saved both games of a doubleheader against them, finishing the season with 46 saves, and breaking the major league record shared by Dan Quisenberry and Bruce Sutter. The record would stand until Bobby Thigpen saved 57 games for the Chicago White Sox in 1990, which would also be Righetti's last season with the Yankees. Righetti retained the single-season record for left-handers until 1993, when Randy Myers saved 53 games for the Chicago Cubs; Righetti still owns the AL record for left-handers.

Righetti's teammate, first baseman and defending American League MVP Don Mattingly, came into the last game batting .352, second in the league to Boston's Wade Boggs. With Boggs sitting out the game, Mattingly needed to go 6 for 6 to win the batting title. Although Mattingly would hit a home run in his first at bat and a double later on, he fell short and Boggs won the batting title. Mattingly would be named most outstanding player that year by the press, but fell short to Boggs' teammate Roger Clemens in the AL MVP voting.

Despite Righetti's pitching on the last day of the season, the Red Sox still won the division and marched on in the playoffs. The Red Sox faced the Yankees' cross-town rivals, the New York Mets, in the World Series. ''The New York Times'' called the series a "painful series". ''Newsday'' called it "woeful days for Yankee fans". Mike Lupica of the ''New York Daily News'' called the series "the World Series that is the Yankee nightmare". Both ''Newsday'' and ''The Boston Globe'' said there were Mets T-shirts saying "Steinbrenner's nightmare," referring to Yankees owner George Steinbrenner. John Powers of the ''Globe'' quoted Claire Smith, who covered the Yankees for the ''Hartford Courant'', as having said "this really is the World Series of the nightmares".

In Game 6 of the World Series, Boston (leading the series 3–2) took a 5–3 lead in the top of the 10th inning. In the bottom half of the inning, Red Sox reliever Calvin Schiraldi retired the first two batters, putting the team within one out of winning the World Series. The Mets, however, scored three runs, tying the game on a wild pitch from Bob Stanley and winning it when Boston first baseman Bill Buckner allowed a ground ball hit by the Mets' Mookie Wilson to roll through his legs, scoring Ray Knight from second base. In Game 7, the Red Sox took an early 3–0 lead, only to lose 8–5. The collapses in the last two games prompted a series of articles by George Vecsey of ''The New York Times'' fueling speculation that the Red Sox were "cursed".

The 1987 season saw rivalry at the end of the season, as on September 29, Yankees' first baseman Don Mattingly set an MLB record by hitting his sixth grand slam home-run of the season against the Red Sox. The competitiveness of the teams continued the following year. Co-captains Ron Guidry and Willie Randolph had led the Yankees to first place two weeks after the All-Star break. On July 28, the Yankees fell out of first place, and the Red Sox won their second division title in three years. Boston went on to face the Oakland Athletics in the 1988 American League Championship Series, but would end up getting swept.

1990–1995

In the early to mid-1990s, the two teams were seldom equally good. The Yankees had the worst record in the American League when the Red Sox won their division title in 1990. In 1992, both teams finished at or near the bottom of the AL East.

In 1990, ''Boston Globe'' columnist Dan Shaughnessy wrote a book titled ''The Curse of the Bambino'', criticizing the Red Sox for the sale of Babe Ruth, and publicized the curse. When the Red Sox were at Yankee Stadium during a weekend in September 1990, Yankees fans started to chant "1918!" to taunt the Red Sox, reminding them of the last time they won a World Series. Each time the Red Sox were at Yankee Stadium afterward, demeaning chants of "1918!" echoed through the stadium. Yankees fans also taunted the Red Sox with signs saying "1918!", "CURSE OF THE BAMBINO", pictures of Babe Ruth, and wearing "1918!" T-shirts each time they were at the Stadium.

On June 6, 1990, before a Yankees–Red Sox game at Fenway Park, the Yankees fired Bucky Dent as their manager, making Fenway Park the scene of his worst moment as manager, although he had his greatest moment as a player there. Red Sox fans felt retribution as Dent was fired on their field, while players on the Yankees, including former Red Sox catcher Rick Cerone and Mattingly felt Dent was used as a scapegoat. Dan Shaughnessy criticized Steinbrenner for firing Dent in Boston and said he should "have waited until the Yankees got to Baltimore" to fire Dent. He said that "if Dent had been fired in Seattle or Milwaukee, this would have been just another event in an endless line of George's jettisons. But it happened in Boston and the nightly news had its hook." He also said that "the firing was only special because...it's the first time a Yankees manager...was purged on the ancient Indian burial grounds of the Back Bay." However, Yankees television analyst Tony Kubek blasted at Steinbrenner for the firing in a harsh, angry way. At the beginning of the broadcast of the game on MSG Network, he said to Yankees television play-by-play announcer Dewayne Staats, "George Steinbrenner...mishandled this. You don't take a Bucky Dent (at) the site of one of the greatest home runs in Yankee history and fire him and make it a media circus for the Boston Red Sox." He then stared defiantly on camera and said to Steinbrenner, "You don't do it by telephone, either, George. You do it face to face, eyeball to eyeball...If you really are a winner, you should not have handled this like a loser." He then said, angrily, "George, you're a bully and a coward." He then said that "What all this does, it just wrecks George Steinbrenner's credibility with his players, with the front office and in baseball more than it already is–if that's possible. It was just mishandled." The firing of Dent shook New York to its core and the Yankees flagship radio station then, WABC, which also criticized the firing, ran editorials demanding that Steinbrenner sell the team.

The 1993 season saw long-time Red Sox fan favorite Wade Boggs defect to the Yankees after eleven seasons with Boston. Later in September 1993, the Yankees defeated Boston at Yankee Stadium via a last-moment reprieve. Trailing 3–1, Mike Stanley's apparent fly out with two outs in the ninth was nullified by a fan running onto the field prior to the pitch being thrown. The umpire had called time and when play resumed, Stanley singled. The Yankees would rally to score three runs and win on a Mattingly single.

The Yankees' 1980s demise and downfall continued into the early 1990s and was at its frustrating peak in 1994, when they finished with the best record in the American League in a season that was prematurely halted by the 1994–95 Major League Baseball strike, which left New York sports fans disappointed that Mattingly had not played in a postseason despite being poised to do so that year. At that time, he led active players in both games played and at-bats without participating in a postseason game. Throughout October, the news media added to the embarrassment when they often made references to dates that games in the World Series would have been played. That year, the Yankees and Red Sox would have finished the season against each other at Fenway Park. Both managers, Buck Showalter of the Yankees and Butch Hobson of the Red Sox, who made their managerial debuts against each other, were fired as a result of or during the strike.

The strike was the harbinger of the 1995 season for the Yankees. Although the Red Sox jumped out to a fast start and finished the season in first place, the Yankees were not serious contenders for the division title. With the Yankees clinching the inaugural American League Wild Card on the last day of the season, the Yankees and Red Sox reached the post-season in the same season for the first time. Before the postseason began, Mattingly contemplated about the first-ever playoff series in the rivalry, saying, "That would be pretty cool. It wouldn't hurt the rivalry any. There'd be a few deaths...just kidding". Both teams lost in separate ALDS series, with the Red Sox being swept by the Cleveland Indians and the Yankees losing in five games to the Seattle Mariners. For the Yankees, the loss led to another post-strike fallout: both Showalter and general manager Gene Michael were fired as a result of the loss. Similarly, the firing of Michael as Yankees manager and the loss in the 1981 World Series were fallouts from the strike that year. In fact, the 1981 strike was antecedence to the Yankees' demise and downfall of the 1980s and 1990s and the strike in 1994 was part of that demise.

1996–2003: Yankees dominance and first postseason meetings

Late 1990s: Yankees dynasty

A year after captain Don Mattingly's retirement in 1995, the Yankees won the 1996 World Series. It was their first in 18 years and the first of former Red Sox player Wade Boggs' career. Boggs celebrated the victory with a memorable moment of jumping on the horse of a NYPD officer during the celebration.

The Yankees had one of the greatest seasons in baseball history in 1998. The Yankees won a then-AL record 114 games and the season culminated in a win over the San Diego Padres in the 1998 World Series. The Red Sox, too, made the playoffs in 1998, but as a Wild Card, they did not seriously contend for the division title. They lost their ALDS.

About four months after victory, the Yankees traded fan favorite David Wells to the Toronto Blue Jays for Roger Clemens, a fan favorite with the Red Sox between 1984 and 1996. Clemens was coming off two consecutive season with the Blue Jays where he had won both the pitching triple crown and the Cy Young Award in both 1997 and 1998.

Once the 1999 season started, a moment of peace occurred between the fans. Yankees manager Joe Torre returned to Fenway Park for his first game following a battle with prostate cancer. While the managers were exchanging lineup cards, the Boston crowd gave Torre a long standing ovation, to which he tipped his cap. Good relations were seen during the All-Star Game at Fenway Park. Yankees manager Joe Torre, manager for the American League team, replaced starting shortstop Nomar Garciaparra of the Red Sox with Derek Jeter. Garciaparra received a standing ovation from the fans after Jeter came in to replace him (they also embraced each other at this time). Later in the game, when he came to bat, Jeter gave Garciaparra a tribute by mimicking his batting stance. Nine years later, in a similar fashion, Red Sox manager Terry Francona managed the American League team at the All-Star Game at Yankee Stadium, in the stadium's final season.

On September 10, 1999, Chili Davis' second-inning home run was the only hit by the Yankees against Pedro Martínez, who struck out 17 Yankees—the most strikeouts against a Yankees team ever in a nine inning game. Martínez retired the last 22 batters after giving up the home run, including striking out eight of the final nine batters. The teams finished first and second in their division and both made the playoffs in the same season. This led to the very first post-season meeting in the longtime rivalry.

1999 ALCS: First postseason meeting

In 1999, the Yankees and Red Sox faced each other for the first time in the ALCS. The Yankees were the defending World Series champions, while Boston had not appeared in the ALCS since 1990. The Yankees won Game 1 on a 10th-inning walk-off home run by Bernie Williams off Boston reliever Rod Beck. Intensity built up due to this historic, first-ever postseason meeting between the two longtime rivals. The Yankees would win the first two games at home with 7th-inning comebacks.

The lone bright spot for the Red Sox came in Game 3 at Fenway Park, in what had been a much anticipated pitching match-up of former Red Sox star Roger Clemens, who was now with the Yankees, and Boston ace Pedro Martínez. Martínez struck out twelve and did not allow a run through seven innings of work; Clemens was hit hard, giving up five earned runs and only lasting two innings of a 13–1 Red Sox victory. The Yankees rebounded to win Games 4 and 5, clinching the American League pennant and advancing to the World Series, where they swept the Atlanta Braves. The loss to Pedro Martínez was the Yankees' only postseason loss, as the team went 11–1.

The following year at Fenway Park, the Yankees beat the Red Sox, 22–1, handing Boston its most lopsided home loss ever. The Yankees scored 16 total runs in the 8th and 9th innings. The Yankees lost 15 of their final 18 games that season and finished with a record of 87–74, but the Red Sox failed to catch up and finished 2.5 games out of first to lose another division title to the Yankees. Despite having the lowest winning percentage of any postseason qualifier in 2000, the Yankees won their third consecutive World Series and 26th overall, in the first Subway Series since 1956, over their cross-town rivals, the New York Mets, in 5 games.

A year later, David Cone

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