The feud between the Boston Red Sox and New York Yankees dates back over a century, featuring curses, brawls and heartbreaks galore. The Yankees-Red Sox rivalry took on new life in the 1990s, though, with the advent of the Wild Card Era. Instead of one team from each division making the MLB playoffs, finally division rivals could face off in the postseason.
That set the stage for the Boston and New York to go head-to-head when it mattered most, instead of just during September pennant races. Both AL East squads made it in as Wild Cards in 2025, for instance, ceding the division crown to the Toronto Blue Jays. As a result, the Red Sox and Yankees are going head-to-head in a best-of-three AL Wild Card Series with a spot in the ALDS up for grabs.
Boston won the head-to-head series 9-4 in the regular season. New York, however, still has an MLB-record 27 World Series to lord over their bitter rivals.
Here is a quick look back at how the Red Sox and Yankees have fared against each other in past Octobers:
1999 ALCS
NYY def. BOS 4-1
The very first postseason meeting between the Red Sox and Yankees didn’t occur until just before the turn of the millennium. Technically, their tiebreaker for the 1978 AL East title didn’t count as a playoff game, even though it was a winner-takes-all game No. 163.
The 1999 ALCS didn’t live up to that historic showdown, even if it was a relatively competitive series. New York claimed Game 1 on Bernie Williams’ walk-off home run, then went up 2-0 after eking out a one-run win in Game 2. Boston battled back by winning Game 3, riding a Pedro Martínez gem to a 13-1 victory, only for the Yankees to answer with 9-2 and 6-1 wins and punch their ticket back to the World Series.
New York went on to sweep the Atlanta Braves and win their third title in four years.
2003 ALCS
NYY def. BOS 4-3
For as wild as the back-and-forth battle between the Red Sox and Yankees was in the 2003 ALCS, the series will always be remembered for Game 7.
Boston was up 5-3 midway through the eighth inning when Martínez started to show signs of slowing down. Manager Grady Little left his ace in the game, though, and New York stormed back to tie things up. Then, in the bottom of the 11th, Aaron Boone took Tim Wakefield deep for the walk-off homer.
The Yankees were unable to win the World Series that time around, but it was still their sixth trip there in eight years. The Red Sox, meanwhile, hadn’t even been to a Fall Classic since 1986.
2004 ALCS
BOS def. NYY 4-3
The Yankees were well on their way back to the World Series, having taken a 3-0 lead over the Red Sox in the 2004 ALCS. Even late into Game 4, it looked like Boston was done.
But down one in the bottom of the ninth, Kevin Millar drew a walk against legendary closer Mariano Rivera. Dave Roberts came in as a pinch-runner, then swiped second. Bill Mueller drove him in with a single to center, forcing extra innings in the process. In the bottom of the 12th, David Ortiz came through with a walk-off homer of his own, keeping the Red Sox alive.
It took another 14 innings for Boston to make it through Game 5, setting up Curt Schilling’s “Bloody Sock Game” in Game 6. Game 7 wasn’t all that close, as the Red Sox blew out the Yankees 10-3 in the Bronx. They proceeded to sweep the St. Louis Cardinals in the World Series a week later, breaking the Curse of the Bambino after 86 years.
2018 ALDS
BOS def. NYY 3-1
While the 2018 Red Sox were one of the most dominant regular season teams in MLB history, the Yankees gave them trouble right out of the gates. Boston nearly blew a 5-0 lead in Game 1 before winning 5-4, then New York stole Game 2 on the road 6-2. That night, Aaron Judge left Fenway Park blasting Frank Sinatra’s “New York, New York.”
The Red Sox responded with a 16-1 win in Game 3, then Craig Kimbrel held strong in Game 4 to secure the 4-3 win and the series victory. While popping champagne in the visitor’s clubhouse at Yankee Stadium, the Red Sox played “New York, New York” over the speakers, trolling Judge and their longtime rivals.
Boston went on to beat the Houston Astros in the ALCS, then the Los Angeles Dodgers in the World Series. It marked their fourth title in 15 years, all while New York had claimed just one in that same span.
2021 AL Wild Card Game
BOS def. NYY 1-0 (6-2)
The single-elimination Wild Card Game is a thing of the past, with the playoff format changing after the 2021 postseason. Luckily for baseball fans everywhere, we got to witness the Red Sox and Yankees face off in the do-or-die playoff game just before it was ushered into extinction.
The Green Monster saved Boston from a Giancarlo Stanton home run in the first inning, even if he came through with a solo shot in the ninth. The Red Sox had created more than enough cushion by then, though, thanks to home runs from Xander Bogaerts and Kyle Schwarber, plus three RBIs from Alex Verdugo. Nathan Eovaldi shoved against his former team, continuing to build out his resume as a shutdown playoff ace. Gerrit Cole, meanwhile, got chased off the mound in just 2+ innings despite being the highest-paid pitcher on the planet.
Boston fell short against the Houston Astros in the ALCS later that postseason and immediately stumbled into a three-year playoff drought. New York won division titles in 2022 and 2024, only to fall short come October both times.
