Despite their prolonged summer slump, the New York Yankees entered Friday still holding a half-game lead over the rival Boston Red Sox for the AL’s top Wild Card seed.
Although the Yankees and Red Sox still have a chance to swipe the AL East crown from the Toronto Blue Jays, all signs point to the two clashing in the Wild Card Round. The Yankees would be the No. 4 seed and host the No. 5 Red Sox in every game of a best-of-three set to determine who would advance to the AL Divisional Round.
Unfortunately for Yankees fans, the Red Sox have dominated the Yankees all season. Boston entered this weekend’s three-game set having won eight of ten in mostly uncompetitive games.
However, plenty can change when the calendar turns to October. As both teams gear up for the postseason, here’s a look at what to expect in a potential Yankees-Red Sox playoff series.
Have the Yankees and Red Sox met in the postseason before?
Yes, the Yankees and Red Sox have previously met in the postseason. Just ask any Red Sox fans who stayed up to watch Game 7 of the 2003 ALCS.
20 Years Ago Today: Aaron Bleepin' Boone hits a dramatic 11th inning walk-off HR vs. the Red Sox in Game 7 of the #ALCS to send the #Yankees to the World Series! (October 16, 2003) #MLB #History #Postseason pic.twitter.com/l6G3JPQyh8
— Baseball by BSmile (@BSmile) October 16, 2023
Before we get to the present, let’s take a quick trip through baseball history. Only one team in each league made the postseason — AKA, the World Series — from 1903 through 1968. When baseball expanded to two divisions per league in 1969, the sport moved to a five-game League Championship Series featuring the East and West division winners; it’s not totally relevant here, but the LCS moved from five to seven games in 1985.
In short, the Yankees and Red Sox could not meet in the playoffs until 1994 at the earliest, when each league moved to three divisions and adopted the Division Series; MLB previously used the LDS in 1981 after a strike canceled roughly a month of play. Of course, the 1994 season ended prematurely with its own strike, so we didn’t see our first LDS since 1995.
Then came 1999, when Derek Jeter’s Yankees battled Pedro Martínez’s Red Sox in the ALCS. As of September 2025, here’s what the Yankees-Red Sox postseason history looks like:
Series | Winner | MVP | Did winner win World Series? |
|---|---|---|---|
1999 ALCS | New York Yankees (4-1) | Orlando Hernández, SP | Yes |
2003 ALCS | New York Yankees (4-3) | Mariano Rivera, CP | No |
2004 ALCS | Boston Red Sox (4-3) | David Ortiz, 1B/DH | Yes |
2018 AL Wild Card Round | Boston Red Sox (3-1) | N/A | Yes |
2021 AL Wild Card Game | Boston Red Sox won, 6-2, in one-game playoff | N/A | No |
Fittingly, the Red Sox and Yankees are tied, 12-12, in the postseason. Remember: the 1978 Bucky Dent game was not a playoff game. It was instead a one-game tiebreaker to decide the AL East.
What should we expect from a Yankees-Red Sox playoff series?
Carlos Narváez makes it a 7-run 9th inning for the @RedSox! pic.twitter.com/VeskVLnZ11
— MLB (@MLB) August 23, 2025
Considering the legacies of the 2003 and 2004 ALCS, it’s strange to think how uncompetitive the Yankees and Red Sox’s most recent postseason meetings were. The Red Sox had no issues dispatching the Yankees in 2018, a series perhaps best remembered for Aaron Judge taunting the Red Sox by playing “New York, New York” from a boombox while leaving Fenway Park after Game 2. Boston got its revenge by sweeping the two games at Yankee Stadium and returning the favor with Frank Sinatra crooning.
As for the 2021 Wild Card Game, the Red Sox roughed Gerrit Cole up for three runs in two-plus innings. It was an evening to forget for Yankees fans, though they could at least take solace in knowing the loss marked the end of the Gary Sánchez era.
How much does history matter here? In some weird way, it matters both more and less than you’d think. Both teams are radically different than the ones that met in October 2021, though Boone and Cora are obviously still the managers. And while the Yankees-Red Sox rivalry is still considered one of the greatest in sports history, fans on both sides tend to agree the series has lacked its luster for quite some time.
Assuming that these two meet in the Wild Card Round, we expect the Red Sox to take advantage of the Yankees’ poor defense, baserunning, and an inconsistent bullpen. We’ll obviously see what the odds are, though we’re sure the Red Sox will be significant favorites at home or on the road.