The New York Yankees sent home the Boston Red Sox after an epic performance from Cam Schittler, a rookie starting pitcher who grew up in Boston and is now sending his childhood team home for the offseason. It was an incredible three-game series that was must-see TV every night.
It’s the latest chapter in a rivalry that is more than 100 years old. Imagine hating someone for a century. That’s what’s happening between Boston and New York, at least when it comes to their baseball team.
There is no bigger rivalry in baseball, and it might be the biggest rivalry in sports. There are 162 games in a baseball season, but both Yankees fans and Red Sox fans circle these games on the calendar. In the playoffs, beating their rival means just a little bit more.
It meant the world that the Red Sox beat the Yankees on the way to ending their World Series curse in 2004. It was imperative that the Yankees spent years extending that curse with a personal touch. When looking at the 100 greatest players in the history of baseball, we’d say at least half of them played for one of these two franchises. And they hated each other.
But this rivalry has some moments that continue to this day. And the rivalry started with the worst trade in the history of sports.
1. December 26, 1919
Boston Red Sox sell Babe Ruth to the New York Yankees
It’s the greatest deal in the history of sports. The Boston Red Sox were in a dire situation after bad business investments and struggling attendance during the war severely impacted the bottom line of the Red Sox, despite being a title contender every year and winning the AL pennant in 1918. The Yankees approached the Red Sox after Babe Ruth asked for a raise, and a deal was struck.
The Yankees sent the Red Sox $100,000 in four payments and got Ruth in return. There were other monetary clauses in the deal (including a reported 6% interest and a large loan that included a mortgage on Fenway Park), but the main part of the deal was the cash payment. The Big Bambino did not take kindly to being sent to the Yankees.
Red Sox owner Harry Frazee called Ruth “selfish” after the deal was struck, and the press was obsessed with the story. There were opinions all over the map. But one thing was clear: baseball at the Polo Grounds, and eventually the Bronx, was about to get a whole lot better.
Ruth dominated for the Yankees, creating the Murderer’s Row with Lou Gehrig and a few other Hall of Famers. They won four World Series with Ruth in the lineup, and he won the 1923 AL MVP. He also became the face of the league, and the Yankees became the most popular franchise in sports. That continues today with the Yankees being worth $8 billion according to CNBC evaluations. Not bad for a roughly $100,000 investment.
2. August 1, 1973
The Fight in Fenway Park
A lot happened between the Ruth trade and the 1970s in this rivalry. Red Ruffin went from an also ran in Boston to a Hall of Famer in New York. The Ted Williams-Joe DiMaggio rivalry within the rivalry, including a rumor that the Yankees and Red Sox came very close to trading the two Hall of Famers for each other. Joe McCarthy coming out of retirement, the 1949 pennant, and a few fights, but there was no bigger fight than the one behind the cachers who were driving this team.
Thurmon Munson was expecting a squeeze bunt, so he sprinted towards home on August 1st, 1973. Gene Michael missed the bunt entirely, and it became an attempted steal home. Since Carlton Fisk already had the ball, he figured it was an easy out. Nope.
Munson drilled Fisk, and everything broke loose. The benches cleared, and an actual fight was on the field. Munson punched Fisk in the face, and it became a melee.
Both benches cleared, and it looked like the Royal Rumble. Both Fisk and Munson were ejected from the game, and the rivalry clearly had more heat behind it than it had in years.
3. October 2, 1978
Bucky @%$&*! Dent
The Yankees-Red Sox rivalry remained intense throughout the 1970s, as both teams were really good and competing for chances to go to the World Series. The Red Sox got to go in 1975, while the Yankees went in 1976 and 1977. And this made 1978 special. The Red Sox and Yankees hadn’t played in a playoff series at this point (because it was nearly impossible), but the two faced off in a one-game playoff at the end of the 1978 season.
This was in the middle of the Billy Martin drama, as he was fired in July despite coming off a World Series victory. On July 19th, the Yankees trailed the Red Sox by 14 games. It was a lost season in the Bronx Zoo. The Red Sox faltered for the rest of the season, and the Yankees chipped away until officially tying them after a four-game sweep in September. At the end of the season, the standings remained tied.
After a pitcher’s duel between Ron Guidry and Mike Torrez, Bucky Dent came up in the seventh inning with the Yankees trailing and two men on. He tipped a pitch that hit him in the ankle, and a pause in the game allowed Mickey Rivers (who often shared a bat with Dent) to switch the bats.
On the next pitch, Dent got a pitch in his wheelhouse. He squared the barrel of the bat, and he launched a ball over the Green Monster. It was his 23rd career home run, and it was the only one he needed to become a legend. The Yankees eliminated the Red Sox, and they went on to win another World Series.
4. October 13, 1999
Yogi’s speech and Bernie’s walkoff
“Relax. We’ve been beating these guys for 80 years." Those were the words of legendary Yankees catcher Yogi Berra, who came to speak to the team before Game 1 of the 1999 ALCS. The Yankees were in dynasty mode, and the Red Sox were desperately trying to play spoiler. The rivalry was regaining steam as both teams had superstars up and down the lineup and rotation. However, 1999 was not the Red Sox year.
This was the first official playoff matchup between the Red Sox and Yankees in history. The two powerhouse organizations now had a Wild Card to get both teams in the playoffs, and it was going to be a series we saw a lot. And it started with Berra’s words, which went to Bernie Williams, the Yankees’ star center fielder. He was reportedly nervous before the series, but those words must have done wonders.
El Duque Orlando Hernandez got tapped for three runs in the first two innings of Game 1, putting the Yankees behind from the start. The Yankees would eventually tie the game, and the Red Sox didn’t score again all game.
With the game in extra innings, Bernie Williams found his chance to release his nervous energy into a baseball. Williams led off the inning and crushed a home run to send the Yankees home happy. The Yanks dominated the rest of the series, as the Red Sox looked overmatched and had a chance to steal one in the Bronx, but they failed and lost the series in 5.
5. October 16, 2003
Aaron Boone sends New York to the World Series
Older Red Sox fans still talk about October 2nd as if it’s this dreaded anniversary because of Bucky Dent. Younger Red Sox fans would talk about October 16th. The game was crazy. It was an incredible matchup of Roger Clemens versus Pedro Martinez. Clemens struggled early, giving up a two-run home run to Trot Nixon in the second and giving up four runs in fewer than four innings.
After two Jason Giambi solo home runs, the Yankees were down 4-2, which became 5-2 on a David Ortiz home run. Then, Pedro came out in the eight. He allowed hits to Jeter and Bernie Williams to make it 5-3. Grady Little came out and saw if he needed to replace his ace. He left him in, and disaster struck. Hideki Matsui hit a double, then Jorge Posada hit another one to tie the game.
That set up the 11th inning. Red Sox starter and knuckleballer Tim Wakefield was on in relief. Aaron Boone came up to bat, but before he hit the batter’s box, hitting coach Willie Randolph had something to tell him. “You’re my sleeper pick. You’re the x-factor of this series.”
Minutes later, Wakefield hung a knuckler to Boone across the plate, Boone swung hard, and into the night and the left field seats, the Yankees were going to the World Series.
6. February 16, 2004
Alex Rodriguez Trade
The year 2004 was the most consequential to this rivalry. It started before the season even took place. After losing to the Yankees in the most heartbreaking fashion, the Red Sox moved pieces to get Alex Rodriguez. At least, they thought they did. The Red Sox asked Rodriguez to make some salary concessions in the deal, and the MLB Players’ Association ended the deal.
Aaron Boone, of walkoff home run fame, got injured playing basketball in the offseason and was going to miss the entire 2003 season. So, here come the Yankees, swooping in and taking Rodriguez from under the Red Sox nose. They thought they had their superstar to build around for the next decade. Instead, he was changing his number (3 was retired for Babe Ruth) and switching positions (Derek Jeter was already at shortstop and the Yankees needed a third baseman).
Rodriguez put jumper cables on this rivalry. He was hated amongst the Red Sox fanbase. Don’t get us wrong, Red Sox fans hated the likes of Paul O’Neill, Derek Jeter, Bernie Williams, and other Yankees greats, but there was an underlying respect with those players. Rodriguez brought something different in them.
There were multiple fights with ARod and the Red Sox, including the famous one he had with Jason Varitek, and there was Rodriguez slapping the ball out of Bronson Arroyo’s hand, and it all started with the February trade that was supposed to be Boston.
7. July 1, 2004
Derek Jeter dives into the stands
There are not many regular-season moments on this list, but nobody is going to say that the Derek Jeter dive into the stands doesn’t define this rivalry. It was a steamy July night at Yankees Stadium, and the two teams were embroiled in a race for the AL East, as had been the norm for a few years at this point. This game was important, as the Red Sox were trying to avoid a series sweep and the Yankees were trying to bury their rivals under an 8 ½ game lead. Prior to the dive, it was one of the greatest games you’ll ever see. The score changed multiple times, Alex Rodriguez got the rare 5-3 double play to keep extra innings going. Keith Foulke got out of his own bases loaded jam.
Then came the 12th inning. Tanyon Sturtze struggled in relief of Mariano Rivera, who already pitched two innings. There were two men on when Trot Nixon popped a ball up near the foul line. Jeter sprinted as fast as we’ve ever seen him run, caught the ball at an angle we didn’t know shoulders allowed, then flew into the third row of seats.
Rodriguez had his hands on his head. The announcers were going crazy after the umpire put up an emphatic “out” sign. The Stadium crowd was going bonkers, and Jeter walked away bloody and battered but successful.
The next inning, backup catcher John Flaherty made the dive worth it, walking off the game and setting up what was a microcosm of the rivalry at this point. The Yankees always find a way. At least, that’s the story up until July 1, 2004.
8. October 17, 2004
Dave Roberts steals second
Can you think of a more important steal of second base? With the Red Sox down one in the bottom of the ninth inning and Mariano Rivera, the greatest closer of all time, on the mound, Dave Roberts got on first with no outs. The Red Sox traded for Roberts in the middle of the season, and his prowess on the bases was a big reason why. This was the moment that Theo Epstein got Roberts for.
Roberts took off on the first pitch, and Posada’s throw was just off enough that Jeter couldn’t apply the tag in time. Roberts was safe, and now the tying run was in scoring position.
This was Game 4. The Yankees were up in the series 3-0. The Red Sox were just trying to survive at this point while also giving their fans something to keep hope. It was in Fenway Park, and their backs were against the wall. It wasn’t the first time, but it would be the last time they had the feeling of dread that came from being cursed. It all started with Roberts’ steal.
Nixon hit a ball up the middle, and Williams’ throw was nowhere near in time. The game was tied, and the Red Sox had hope. Thanks to Roberts' steal. This was the moment that turned the dial in the Red Sox’s favor, and it never turned the other way.
9. October 19, 2004
The Bloody Sock Game
Curt Schilling had beaten the New York Yankees before. He was a part of the one-two punch that helped the Arizona Diamondbacks win the 2001 World Series. He paired with Randy Johnson to win possibly the greatest series in baseball history. Now, he was trying to make history again. If it wasn’t for that pesky tendon in his ankle.
See, it was Game 6 of the ALCS, and the Red Sox had swung the momentum already. Now, the pressure was on the Yankees, and the game was in Fenway. Schilling got beat up in Game 1, but this was a different series. That felt like a month ago at this point. Schilling had a chance to push the Yankees to the edge.
What didn’t feel like a month ago was Schilling’s torn tendon sheath in his right ankle. The injury happened in Game 1, and doctors weren’t able to keep it closed during his pitching. Schilling went out anyway and allowed just one run in seven innings pitched. All while his sock started to turn a new shade of red.
Knowing the sock was going to be a message on his cleat in the World Series. He wrote “K ALS,” referring to the disease also referred to as “Lou Gehrig’s disease.” The Bloody Sock Game lives in Yankees fans' minds to this day. They had a chance to stop the comeback against an injured pitcher, but they failed. Boston destroyed the Yankees in Game 7, and the Cardinals didn’t stand a chance in the World Series. The curse was over, and the Red Sox were now the winners of the rivalry.
10. October 1-3, 2025
Epic Three-Game Series
Plenty has happened since the Red Sox won that first World Series of this era. Boston actually tilted the scales towards themselves, winning the 2018 ALDS against the Yankees in four games and winning three more titles. They also played in a winner-take-all Wild Card Game in 2021, and the Red Sox dominated, beating Gerrit Cole starting in the first inning and never letting up.
However, there has been no series that feels like the Red Sox-Yankees rivalry is back like the 2025 series. It was just three games, but all three games had incredible stories and amazing tenacity. The Red Sox came in with a severely undermanned lineup, trading Yankees killer Rafael Devers during the season and losing superstar rookie Roman Anthony to an injury.
That’s what made Garrett Crochet’s Game 1 performance so special. The Red Sox knew they needed Game 1 to stay alive, and the Yankees put out Max Fried. Both Fried and Crochet were incredible, putting up Cy Young-level performances. Unfortunately for Yankees fans, Aaron Boone took Fried out to avoid a third go around in the lineup. Alex Cora trusted his starter, and he went 117 pitches through 7 ⅔ innings. Aroldis Chapman came in and loaded the bases in the ninth with no outs, and the Yankees scored exactly no runs on that. The game was epic.
Then, Game 2 comes down to one play. With the game tied at three in the eighth inning, Jazz Chisolm, who was benched in Game 1, walked to start the inning. Catcher Austin Wells hit a rocket down the line, but he was held to a single. Chisholm was not held at all. He sprinted around the bases, getting from first to home in around 9.16 seconds, and scored within inches of the tag to give the Yankees a 4-3 lead, which held for the rest of the game.
In the deciding Game 3, it was all about Yankees rookie Cam Schlittler. The 24-year-old grew up rooting for the team in Fenway, but he was tasked with ending their season in Yankee Stadium. He dominated with his 101 MPH fastballs. He struck out 12 batters en route to delivering a series win, and the Red Sox-Yankees rivalry is back and better than ever.