The Boston Red Sox and New York Yankees are getting ready to meet in the playoffs again.
Boston will travel to Yankee Stadium for a best-of-three American League Wild Card Series beginning Tuesday, September 29.
It will mark the seventh postseason matchup between the two longtime rivals.
Despite more than a century of history between the teams, every official postseason matchup between the Red Sox and Yankees has come since 1999.
Here is a look at every previous Red Sox-Yankees playoff matchup.
1999 American League Championship Series
The first postseason meeting between the Red Sox and Yankees came in 1999.
New York won the American League Championship Series four games to one.
The Yankees won the first two games at Yankee Stadium before the series moved to Boston.
The Red Sox responded with a 13-1 win in Game 3. Pedro Martinez threw seven scoreless innings while Boston knocked former Red Sox ace Roger Clemens out of the game early.
It was the Yankees' only loss of the entire 1999 postseason.
New York won the next two games at Fenway Park to finish the series in five games.
The Yankees then swept the Atlanta Braves in the World Series.
Series winner: Yankees, 4-1
2003 American League Championship Series
The Red Sox and Yankees met again four years later.
This one went seven games.
Boston led Game 7 by a 4-0 score and still held a 5-2 lead in the eighth inning.
The Yankees rallied against Pedro Martinez to tie the game.
The game remained tied until the bottom of the 11th inning.
Aaron Boone hit the first pitch he saw from Tim Wakefield over the left-field wall for a walk-off home run.
The homer sent New York to the World Series and became one of the most famous moments in Yankees-Red Sox history.
Boone later became manager of the Yankees.
Series winner: Yankees, 4-3
2004 American League Championship Series
One year later, the Red Sox got another chance.
It initially looked even worse for Boston.
The Yankees won the first three games of the American League Championship Series. New York crushed Boston 19-8 at Fenway Park in Game 3.
No Major League Baseball team had ever come back from a 3-0 deficit to win a best-of-seven postseason series.
Then Boston did it.
The Red Sox trailed in the ninth inning of Game 4 before Kevin Millar walked and Dave Roberts stole second base. Bill Mueller drove Roberts home to tie the game.
David Ortiz won it with a walk-off home run in the 12th inning.
Ortiz delivered another walk-off hit in Game 5.
Boston won Game 6 at Yankee Stadium behind Curt Schilling and his famous bloody sock performance.
The Red Sox finished the comeback with a 10-3 win in Game 7.
Boston then swept the St. Louis Cardinals to win its first World Series since 1918.
The Red Sox remain the only MLB team to overcome a 3-0 deficit and win a best-of-seven postseason series.
Series winner: Red Sox, 4-3
2018 American League Division Series
It took another 14 years for the rivals to meet in October.
This time, Boston entered the postseason after winning a franchise-record 108 regular-season games.
The Red Sox won Game 1 at Fenway Park before the Yankees tied the series.
Boston then took control in New York.
The Red Sox crushed the Yankees 16-1 in Game 3 at Yankee Stadium.
Boston finished the series with a 4-3 win the following night.
The Red Sox later beat the Houston Astros in the American League Championship Series and the Los Angeles Dodgers in the World Series.
Series winner: Red Sox, 3-1
2021 American League Wild Card Game
The Red Sox and Yankees finished the 2021 regular season with identical 92-70 records.
That set up a winner-take-all Wild Card Game at Fenway Park.
Boston jumped on Yankees starter Gerrit Cole early.
Xander Bogaerts hit a two-run home run in the first inning. Kyle Schwarber added a solo home run in the third.
Cole lasted just two-plus innings.
Nathan Eovaldi allowed one run over 5 1/3 innings for Boston and the Red Sox won 6-2.
Boston went on to beat the Tampa Bay Rays in the AL Division Series before losing to Houston in the AL Championship Series.
Winner: Red Sox, 6-2
2025 American League Wild Card Series
The rivalry returned to the postseason in 2025.
Boston took Game 1 at Yankee Stadium behind Garrett Crochet, who struck out 11 hitters.
That put the Red Sox one win away from advancing.
New York came back.
The Yankees won Game 2 as the Red Sox struggled defensively before rookie Cam Schlittler took over in Game 3.
Schlittler threw eight scoreless innings and struck out 12 as New York beat Boston 4-0.
The Yankees became the first team under the current Wild Card Series format to lose Game 1 and still win the series.
It was New York's first postseason series victory over Boston since 2003.
Series winner: Yankees, 2-1
What About The 1978 Bucky Dent Game?
The famous 1978 game between the Red Sox and Yankees was not technically a postseason game.
The teams finished the regular season tied for first place in the American League East, forcing a one-game tiebreaker at Fenway Park.
At the time, the game counted as an additional regular-season game.
Boston led 2-0 in the seventh inning when Yankees shortstop Bucky Dent hit a three-run home run over the Green Monster.
New York held on for a 5-4 win.
The Yankees later won the World Series.
Although it does not count as an official postseason matchup, the game remains one of the most famous winner-take-all games in baseball history.
Red Sox-Yankees Playoff Record Entering 2026
The rivalry could hardly be more even entering the 2026 playoffs.
The Yankees have won three postseason matchups:
- 1999 ALCS
- 2003 ALCS
- 2025 Wild Card Series
The Red Sox have also won three:
- 2004 ALCS
- 2018 ALDS
- 2021 Wild Card Game
The Yankees hold a narrow 14-13 advantage in individual postseason games between the teams.
That makes the 2026 Wild Card Series a chance for either franchise to take the lead in postseason series wins against its biggest rival.
The Yankees earned the No. 4 seed in the American League while Boston locked up the No. 5 seed.
New York also won the 2026 regular-season series against Boston, seven games to six.
All games in the best-of-three Wild Card Series will take place at Yankee Stadium.